1-cycloalkylpyrazolyl-benzoyl derivatives

ABSTRACT

The present invention relates to 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I                    
     wherein all variables are as defined in the specification, their agriculturally useful salts, processes for their preparation, and for the use of these compounds or compositions comprising them, for controlling undesirable plants.

This application is a 371 of PCT/EP99/09342 filed Dec. 1, 1999.

The present invention relates to 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I

where:

X is O, NR⁶ or CR⁷R⁸;

Y is O, S, NR⁹ or CR¹⁰R¹¹;

R¹ is nitro, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfonyl or C₁-C₄-haloalkylsulfonyl;

R²,R³,R⁷,R⁸,R¹⁰,R¹¹ are hydrogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl;

or

R³ and R⁶ or R³ and R⁸ or R³ and R⁹ or R³ and R¹¹ together form a bond;

R⁴ is halogen, nitro, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfonyl or C₁-C₄-haloalkylsulfonyl;

R⁵ is hydrogen, halogen or C₁-C₄-alkyl;

R⁶,R⁹ are hydrogen or C₁-C₆-alkyl;

R¹² is hydroxyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₁-C₆-alkylsulfonyloxy, C₁-C₆-alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

R¹³ is a cyclic ring system containing 3 to 14 ring atoms which may be partially or fully halogenated and/or may carry one to three of the following groups: C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy;

R¹⁴ is hydrogen or C₁-C₄-alkyl;

and their agriculturally useful salts.

Moreover, the invention relates to processes for preparing compounds of the formula I, to compositions comprising them and to the use of these derivatives or of compositions comprising them for controlling harmful plants.

Cycloalkyl-substituted pyrazolylbenzoyl derivatives which are substituted in the 3-position of the benzoyl radical by an N-bonded heterocycle or by phenyl are disclosed in the literature, for example in WO 98/42678 and WO 98/52926.

However, the herbicidal properties of the prior art compounds and their compatibility with crop plants may not be entirely satisfactory.

It is an object of the present invention to provide novel, in particular herbicidally active, compounds having improved properties.

We have found that this object is achieved by the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I and their herbicidal action.

Furthermore, we have found herbicidal compositions which comprise the compounds I and have very good herbicidal action. Moreover, we have found processes for preparing these compositions and methods for controlling undesirable vegetation using the compounds I.

Depending on the substitution pattern, the compounds of the formula I may contain one or more chiral centers, in which case they are present as enantiomers or mixtures of diastereomers. The invention provides both the pure enantiomers or diastereomers and their mixtures.

The compounds of the formula I can also be present in the form of their agriculturally useful salts, the kind of salt usually being immaterial. In general, the salts of those cations or the acid addition salts of those acids are suitable whose cations and anions, respectively, do not adversely affect the herbicidal action of the compounds I.

Suitable cations are, in particular, ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium, where, if desired, one to four hydrogen atoms may be replaced here by C₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl, preferably ammonium, dimethylassonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium, di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C₁-C₄-alkanoic acids, preferably formate, acetate, propionate and butyrate.

The organic molecular moieties mentioned for the substituents R¹-R¹² or as radicals on phenyl rings are collective terms for individual enumerations of the individual group members. All hydrocarbon chains, i.e. all alkyl, alkylcarbonyl, haloalkyl, alkoxy, haloalkoxy, alkylcarbonyloxy, alkylsulfonyloxy, alkylthio, haloalkylthio, alkylsulfonyl, haloalkylsulfonyl, alkenyl and alkenyloxy moieties can be straight-chain or branched. Unless indicated otherwise, halogenated substituents preferably carry one to five identical or different halogen atoms. The term halogen represents in each case fluorine, chlorine, bromine or iodine.

Examples of other meanings are:

C₁-C₄-alkyl, and the alkyl moieties of C₁-C₄-alkylcarbonyl and C₁-C₄-alkylcarbonyloxy: for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl;

C₁-C₆-alkyl, and the alkyl moieties of C₁-C₆-alkylcarbonyl and C₁-C₆-alkylcarbonyloxy: C₁-C₄-alkyl as mentioned above, and also, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-3-methylpropyl;

C₁-C₄-haloalkyl: a C₁-C₄-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoramethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromoethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl and nonafluorobutyl;

C₁-C₄-alkoxy: for example methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy;

C₁-C₆-alkoxy: C₁-C₄-alkoxy as mentioned above, and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy;

C₁-C₄-haloalkoxy: a C₁-C₄-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and nonafluorobutoxy;

C₁-C₄-alkylthio: for example methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio and 1,1-dimethylethylthio;

C₁-C₄-haloalkylthio: a C₁-C₄-alkylthio radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2,3-dichloropropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio, heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio, 1-(chloromethyl)-2-chloroethylthio, 1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio and nonafluorobutylthio;

C₁-C₄-alkylsulfonyl (C₁-C₄-alkyl-S(═O)₂-), and the alkylsulfonyl moieties of C₁-C₄-alkylsulfonyloxy: for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl and 1,1-dimethylethylsulfonyl;

C₁-C₆-alkylsulfonyl, and the alkylsulfonyl moieties of C₁-C₆-alkylsulfonyloxy: a C₁-C₄-alkylsulfonyl radical as mentioned above, and also, for example, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl;

C₁-C₄-haloalkylsulfonyl: a C₁-C₄-alkylsulfonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl, 2,2,3,3,3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl, 1-(fluoromethyl)-2-fluoroethylsulfonyl, 1-(chloromethyl)-2-chloroethylsulfonyl, 1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl and nonafluorobutylsulfonyl;

C₃-C₆-alkenyloxy: for example prop-1-en-1-yloxy, prop-2-en-1-yloxy, 1-methylethenyloxy, buten-1-yloxy, buten-2-yloxy, buten-3-yloxy, 1-methylprop-1-en-1-yloxy, 2-methylprop-1-en-1-yloxy, 1-methylprop-2-en-1-yloxy, 2-methylprop-2-en-1-yloxy, penten-1-yloxy, penten-2-yloxy, penten-3-yloxy, penten-4-yloxy, 1-methylbut-1-en-1-yloxy, 2-methylbut-1-en-1-yloxy, 3-methylbut-1-en-1-yloxy, 1-methylbut-2-en-1-yloxy, 2-methylbut-2-en-1-yloxy, 3-methylbut-2-en-1-yloxy, 1-methylbut-3-en-1-yloxy, 2-methylbut-3-en-1-yloxy, 3-methylbut-3-en-1-yloxy, 1,1-dimethylprop-2-en-1-yloxy, 1,2-dimethylprop-1-en-1-yloxy, 1,2-dimethylprop-2-en-1-yloxy, 1-ethylprop-1-en-2-yloxy, 1-ethylprop-2-en-1-yloxy, hex-1-en-1-yloxy, hex-2-en-1-yloxy, hex-3-en-1-yloxy, hex-4-en-1-yloxy, hex-5-en-1-yloxy, 1-methylpent-1-en-1-yloxy, 2-methylpent-1-en-1-yloxy, 3-methylpent-1-en-1-yloxy, 4-methylpent-1-en-1-yloxy, 1-methylpent-2-en-1-yloxy, 2-methylpent-2-en-1-yloxy, 3-methylpent-2-en-1-yloxy, 4-methylpent-2-en-1-yloxy, 1-methylpent-3-en-1-yloxy, 2-methylpent-3-en-1-yloxy, 3-methylpent-3-en-1-yloxy, 4-methylpent-3-en-1-yloxy, 1-methylpent-4-en-1-yloxy, 2-methylpent-4-en-1-yloxy, 3-methylpent-4-en-1-yloxy, 4-methylpent-4-en-1-yloxy, 1,1-dimethylbut-2-en-1-yloxy, 1,1-dimethylbut-3-en-1-yloxy, 1,2-dimethylbut-1-en-1-yloxy, 1,2-dimethylbut-2-en-1-yloxy, 1,2-dimethylbut-3-en-1-yloxy, 1,3-dimethylbut-1-en-1-yloxy, 1,3-dimethylbut-2-en-1-yloxy, 1,3-dimethylbut-3-en-1-yloxy, 2,2-dimethylbut-3-en-1-yloxy, 2,3-dimethylbut-1-en-1-yloxy, 2,3-dimethylbut-2-en-1-yloxy, 2,3-dimethylbut-3-en-1-yloxy, 3,3-dimethylbut-1-en-1-yloxy, 3,3-dimethylbut-2-en-1-yloxy, 1-ethylbut-1-en-1-yloxy, 1-ethylbut-2-en-1-yloxy, 1-ethylbut-3-en-1-yloxy, 2-ethylbut-1-en-1-yloxy, 2-ethylbut-2-en-1-yloxy, 2-ethylbut-3-en-1-yloxy, 1,1,2-trimethylprop-2-en-1-yloxy; 1-ethyl-1-methylprop-2-en-1-yloxy, 1-ethyl-2-methylprop-1-en-1-yloxy and 1-ethyl-2-methylprop-2-en-1-yloxy;

C₃-C₆-alkenyl: prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl, buten-1-yl, buten-2-yl, buten-3-yl, 1-methylprop-1-en-1-yl, 2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, penten-1-yl, penten-2-yl, penten-3-yl, penten-4-yl, 1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl, 3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl, 1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl, hex-1-en-1-yl, hex-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5en-1-yl, 1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl, 1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl, 3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl, 2-ethylbut-1-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl, 1-ethyl-2-methylprop-1-en-1-yl and 1-ethyl-2-methylprop-2-en-1-yl.

The term “cyclic ring system having 3 to 14 ring atoms” denotes: C₃-C₈-cycloalkyl, C₃-C₈-cycloalkenyl, a bi- or tricyclic carbocyclic or heterocyclic ring system having up to 14 ring atoms, where the ring system may be saturated or contain one, two or three double bonds and, in the case of the heterocyclic rings, may contain one to three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur. The “cyclic ring systems having 3 to 14 ring atoms” may be partially or fully halogenated and/or may carry one to three of the following groups:

C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy.

Examples of other meanings are:

C₃-C₆-cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;

C₃-C₈-cycloalkyl: C₃-C₆-cycloalkyl as mentioned above, and also cycloheptyl or cyclooctyl;

C₅-C₆-cycloalkenyl: cyclopentenyl or cyclohexenyl;

C₃-C₆-cycloalkenyl: C₅-C₆-cycloalkenyl as mentioned above, and also cyclopropenyl or cyclobutenyl;

C₃-C₈-cycloalkenyl: C₃-C₆-cycloalkenyl as mentioned above, and also cycloheptenyl or cyclooctenyl;

bi- or tricyclic ring system: for example adamantyl, norbornyl, camphyl, camphenyl or norbornenyl.

The phenyl rings are preferably unsubstituted or carry one to three halogen atoms and/or one nitro group, one cyano group, one or two methyl, trifluoromethyl, methoxy or trifluoromethoxy groups.

Emphasis is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where the variables both on their own and in combination with one another have the following meanings:

X is O, NR⁶ or CR⁷R⁸;

Y is O, S, NR⁹ or CR¹⁰R¹¹;

R¹ is nitro, halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy; particularly preferably halogen, such as fluorine, chlorine or bromine, C₁-C₄-alkyl, such as methyl or ethyl, or C₁-C₄-alkoxy, such as methoxy or ethoxy; with very particular preference chlorine, methyl or methoxy;

R²,R³,R⁷,R⁸,R¹⁰,R¹¹ are hydrogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl; particularly preferably hydrogen, methyl, ethyl, propyl, 1-methylethyl, fluoromethyl or chloromethyl; with very particular preference hydrogen, methyl, ethyl or chloromethyl;

or

R³ and R⁶ or R³ and R⁸ or R³ and R⁹ or R³ and R¹¹ together form a bond;

R⁴ is halogen, nitro, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio or C₁-C₄-alkylsulfonyl; particularly preferably halogen, such as chlorine or bromine, nitro, C₁-C₂-haloalkyl, such as difluoromethyl or trifluoromethyl, C₁-C₂-alkoxy, such as methoxy or ethoxy, C₁-C₂-haloalkoxy, such as difluoromethoxy, chlorodifluoromethoxy or trifluoromethoxy, C₁-C₃-alkylthio, such as methylthio, ethylthio or 1-methyl-1-ethylthio, or C₁-C₃-alkylsulfonyl, such as methylsulfonyl, ethylsulfonyl, 1-methylethylsulfonyl or propylsulfonyl;

R⁵ is hydrogen, halogen or methyl or ethyl; particularly preferably hydrogen, chlorine or methyl; with very particular preference hydrogen;

R⁶, R⁹ are hydrogen or C₁-C₄-alkyl; particularly preferably hydrogen, methyl or ethyl; with very particular preference methyl;

R¹² is hydroxyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₁-C₆-alkylsulfonyloxy, C₁-C₆-alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; particularly preferably hydroxyl, C₁-C₄-alkoxy, C₃-C₆-alkenyloxy, C₁-C₄-alkylsulfonyloxy, C₁-C₄-alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

R¹³ is C₃-C₈-cycloalkyl, C₃-C⁸-cycloalkenyl, a bi- or tricyclic carbocyclic or heterocyclic ring system having up to 14 ring atoms, where the ring system may be saturated or contain one, two or three double bonds and, in the case of the heterocyclic rings, may contain one to three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur. The “cyclic ring systems having 3 to 14 ring atoms” may be partially or fully halogenated and/or may carry one to three of the following groups: C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy;

particularly preferably C₃-C₈-cycloalkyl, C₃-C₈-cycloalkenyl or a bi- or tricyclic carbocyclic ring system which contains up to 14 ring atoms and is saturated or contains one, two or three double bonds, and where the radicals mentioned may be partially or fully halogenated and/or may carry one to three of the following groups: C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy; with very particular preference C₃-C₆-cycloalkyl, C₅-C₆-cycloalkenyl or a bi- or tricyclic carbocyclic ring system selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl or norbornenyl; more preferably C₃-C₆-cycloalkyl; with most preference cyclopropyl;

R¹⁴ is hydrogen or C₁-C₄-alkyl; particularly preferably hydrogen or methyl.

Preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where:

X is O;

R¹ is nitro, halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy; particularly preferably halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy; with particular preference halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with very particular preference chlorine, methyl or methoxy;

R⁴ is halogen, nitro, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio or C₁-C₄-alkylsulfonyl; particularly preferably halogen, such as chlorine or bromine, nitro, C₁-C₂-haloalkyl, such as difluoromethyl or trifluoromethyl, C₁-C₂-alkoxy, C₁-C₂-haloalkoxy, such as difluoromethoxy, chlorodifluoromethoxy or trifluoromethoxy, C₁-C₂-alkylthio, such as methylthio or ethylthio, or C₁-C₂-alkylsulfonyl, such as methylsulfonyl or ethylsulfonyl.

Particular preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is O;

Y is CR¹⁰R¹¹;

R¹ is halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy; particularly preferably halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with very particular preference chlorine, methyl or methoxy;

R²,R³,R¹⁰,R¹¹ are hydrogen, C₁-C₄-alkyl; or R³ and R¹¹ together form a bond; particularly preferably hydrogen, methyl or ethyl; or R³ and R¹¹ together form a bond;

R⁴ is nitro, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; particularly preferably nitro, C₁-C₂-haloalkyl, such as difluoromethyl or trifluoromethyl, C₁-C₂-alkoxy or C₁-C₂-haloalkoxy, such as difluoromethoxy;

R⁵ is hydrogen;

R¹² is hydroxyl, C₁-C₆-alkylsulfonyloxy, C¹-C₆-alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; particularly preferably hydroxyl;

R¹³ is C₃-C₆-cycloalkyl, C₅-C₆-cycloalkenyl or a bi- or tricyclic carbocyclic ring system selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl and norbornenyl; particularly preferably C₃-C₆-cycloalkyl; with very particular preference cyclopropyl.

Most preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is O;

Y is CR¹⁰R¹¹;

R²,R³,R¹⁰,R¹¹ are hydrogen or methyl or ethyl; preferably hydrogen or methyl.

Most preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is O;

Y is CR¹⁰R¹¹;

R²,R¹⁰ are hydrogen or methyl or ethyl; preferably hydrogen or methyl;

R³ and R¹¹ together form a bond.

Particular preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is O;

Y is CR¹⁰R¹¹;

R¹ is halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy; particularly preferably halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with particular preference chlorine, methyl or methoxy;

R²,R³,R¹⁰,R¹¹ are hydrogen or C₁-C₄-alkyl; or R³ and R¹¹ together form a bond; particularly preferably hydrogen, methyl or ethyl; or R³ and R¹¹ together form a bond;

R⁴ is halogen, C₁-C₄-alkylthio or C₁-C₄-alkylsulfonyl; particularly preferably chlorine or bromine, methylthio, ethylthio or 1-methyl-1-ethylthio or methylsulfonyl, ethylsulfonyl, 1-methylethylsulfonyl or propylsulfonyl;

R⁵ is hydrogen;

R¹² is hydroxyl, C₁-C₆-alkylsulfonyloxy, C₁-C₆-alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; particularly preferably hydroxyl;

R¹³ is C₃-C₆-cycloalkyl, C₅-C₆-cycloalkenyl or a bi- or tricyclic ring system selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl and norbornenyl; particularly preferably C₃-C₆-cycloalkyl; with particular preference cyclopropyl.

Most preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is O;

Y is CR¹⁰R¹¹;

R²,R³,R¹⁰,R¹¹ are hydrogen or methyl or ethyl; preferably hydrogen or methyl.

Most preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is O;

Y is CR¹⁰R¹¹;

R²,R¹⁰ are hydrogen or methyl or ethyl; preferably hydrogen or methyl;

R³ and R¹¹ together form a bond.

Preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where the variables have the following meanings:

X is NR⁶;

R¹ is nitro, halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy; particularly preferably halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy; with particular preference halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with very particular preference chlorine, methyl or methoxy;

R⁴ is halogen, nitro, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio or C₁-C₄-alkylsulfonyl; particularly preferably halogen, such as chlorine or bromine, nitro, C₁-C₂-haloalkyl, such as difluoromethyl or trifluoromethyl, C₁-C₂-alkoxy, such as methoxy or ethoxy, C₁-C₂-haloalkoxy, such as difluoromethoxy, chlorodifluoromethoxy or trifluoromethoxy, C₁-C₂-alkylthio, such as methylthio or ethylthio, or C₁-C₂-alkylsulfonyl, such as methylsulfonyl or ethylsulfonyl.

Particular preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is N(C₁-C₆-alkyl); particularly preferably N-methyl, N-ethyl, N-(1-methyl-1-ethyl) or N-propyl;

Y is NR⁹ or CR¹⁰R¹¹;

R¹ is halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy; particularly preferably halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with particular preference chlorine, methyl or methoxy;

R²,R³,R¹⁰,R¹¹ are hydrogen or C₁-C₄-alkyl; or R³ and R⁹ or R³ and R¹¹ together form a bond; particularly preferably hydrogen, methyl or ethyl; or R³ and R⁹ or R³ and R¹¹ together form a bond;

R⁴ is nitro, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; particularly preferably nitro, C₁-C₂-haloalkyl, such as difluoromethyl or trifluoromethyl, C₁-C₂-alkoxy or C₁-C₂-haloalkoxy, such as difluoromethoxy;

R⁵ is hydrogen;

R⁹ is hydrogen or C₁-C₄-alkyl; particularly preferably C₁-C₄-alkyl; with particular preference methyl or ethyl;

R¹² is hydroxyl, C₁-C₆-alkylsulfonyloxy, C₁-C₆-alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; particularly preferably hydroxyl;

R¹³ is C₃-C₆-cycloalkyl, C₅-C₆-cycloalkenyl or a bi- or tricyclic carbocyclic ring system selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl and norbornenyl; particularly preferably C₃-C₆-cycloalkyl; with particular preference cyclopropyl.

Most preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is N-(C₁-C₆-alkyl); particularly preferably N-methyl, N-ethyl, N-(1-methyl-1-ethyl) or N-propyl;

Y is CR¹⁰R¹¹;

R²,R³,R¹⁰,R¹¹ are hydrogen or C₁-C₄-alkyl; preferably hydrogen, methyl or ethyl; particularly preferably hydrogen or methyl.

Most preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is N-(C₁-C₆-alkyl); particularly preferably N-methyl, N-ethyl, N-(1-methyl-1-ethyl) or N-propyl;

Y is NR⁹ or CR¹⁰R¹¹;

R²,R¹⁰ are hydrogen or C₁-C₄-alkyl; preferably hydrogen, methyl or ethyl; with particular preference hydrogen or methyl;

R³ and R⁹ or R³ and R¹¹ together form a bond.

Particular preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is N-(C₁-C₆-alkyl); particularly preferably N-methyl, N-ethyl, N-(1-methyl-1-ethyl) or N-propyl;

Y is NR⁹ or CR¹⁰R¹¹;

R¹ is halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy; particularly preferably halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with particular preference chlorine, methyl or methoxy;

R²,R³,R¹⁰,R¹¹ are hydrogen or C₁-C₄-alkyl; or R³ and R⁹ or R³ and R¹¹ together form a bond; particularly preferably hydrogen, methyl or ethyl; or R³ and R⁹ or R³ and R¹¹ together form a bond;

R⁴ is halogen, C₁-C₄-alkylthio or C₁-C₄-alkylsulfonyl; particularly preferably chlorine or bromine, methylthio, ethylthio or 1-methyl-1-ethylthio or methylsulfonyl, ethylsulfonyl, 1-methylethylsulfonyl or propylsulfonyl;

R⁵ is hydrogen;

R⁹ is hydrogen or C₁-C₄-alkyl; particularly preferably C₁-C₄-alkyl; with particular preference methyl or ethyl;

R¹² is hydroxyl, C₁-C₆-alkylsulfonyloxy, C₁-C₆-alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; particularly preferably hydroxyl;

R¹³ is C₃-C₆-cycloalkyl, C₅-C₆-cycloalkenyl or a bi- or tricyclic carbocyclic ring system, selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl and norbornenyl; particularly preferably C₁-C₆-cycloalkyl; with particular preference cyclopropyl.

Most preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is N-(C₁-C₆-alkyl); particularly preferably N-methyl, N-ethyl, N-(1-methyl-1-ethyl) or N-propyl;

Y is CR¹⁰R¹¹;

R²,R³,R¹⁰,R¹¹ are hydrogen or C₁-C₄-alkyl; preferably hydrogen, methyl or ethyl; with particular preference hydrogen or methyl.

Most preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is N-(C₁-C₆-alkyl); particularly preferably N-methyl, N-ethyl, N-(1-methyl-1-ethyl) or N-propyl;

Y is NR⁹ or CR¹⁰R¹¹;

R²,R¹⁰ are hydrogen or C₁-C₄-alkyl; preferably hydrogen, methyl or ethyl; with particular preference hydrogen or methyl;

R³ and R⁹ or R³ and R¹¹ together form a bond.

Particular preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is NR⁶;

Y is O, S or N-(C₁-C₆-alkyl); particularly preferably O, S or N-methyl, N-ethyl, N-(1-methyl-1-ethyl) or N-propyl;

R¹ is halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy; particularly preferably halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with particular preference chlorine, methyl or methoxy;

R² is hydrogen or C₁-C₄-alkyl; particularly preferably hydrogen, methyl or ethyl;

R³ and R⁶ together form a bond;

R⁵ is hydrogen;

R¹² is hydroxyl, C₁-C₆-alkylsulfonyloxy, C₁-C₆-alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; particularly preferably hydroxyl;

R¹³ is C₃-C₆-cycloalkyl, C₅-C₆-cycloalkenyl or a bi- or tricyclic carbocyclic ring system selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl and norbornenyl; particularly preferably C₃-C₆-cycloalkyl; with particular preference cyclopropyl.

Most preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

R⁴ is nitro, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; particularly preferably nitro, C₁-C₂-haloalkyl, such as difluoromethyl or trifluoromethyl, C₁-C₂-alkoxy or C₁-C₂-haloalkoxy, such as difluoromethoxy.

Most preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

R⁴ is halogen, C₁-C₄-alkylthio or C₁-C₄-alkylsulfonyl; particularly preferably chlorine or bromine, methylthio, ethylthio or 1-methyl-1-ethylthio or methylsulfonyl, ethylsulfonyl, 1-methylethylsulfonyl or propylsulfonyl.

Preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where:

X is CR⁷R⁸;

R¹ is nitro, halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy; particularly preferably halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy; with particular preference halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with very particular preference chlorine, methyl or methoxy;

R⁴ is halogen, nitro, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio or C₁-C₄-alkylsulfonyl; particularly preferably halogen, such as chlorine or bromine, nitro, C₁-C₂-haloalkyl, such as difluoromethyl or trifluoromethyl, C₁-C₂-alkoxy, such as methoxy or ethoxy, C₁-C₂-haloalkoxy, such as difluoromethoxy, chlorodifluoromethoxy or trifluoromethoxy, C₁-C₂-alkylthio, such as methylthio or ethylthio, or C₁-C₂-alkylsulfonyl, such as methylsulfonyl or ethylsulfonyl.

Particular preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is CR⁷R⁸;

Y is O, S or NR⁹;

R¹ is halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy; particularly preferably halogen, such as fluorine, chlorine or bromine, methyl or ethyl, methoxy or ethoxy; with particular preference chlorine, methyl or methoxy;

R²,R³,R⁷,R⁸ are hydrogen or C₁-C₄-alkyl; or R³ and R⁸ together form a bond; particularly preferably hydrogen, methyl or ethyl; or R³ and R⁸ together form a bond;

R⁴ is nitro, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; particularly preferably nitro, C₁-C₂-haloalkyl, such as difluoromethyl or trifluoromethyl, C₁-C₂-alkoxy or C₁-C₂-haloalkoxy, such as difluoromethyloxy;

R⁵ is hydrogen;

R⁹ is hydrogen or C₁-C₄-alkyl; particularly preferably C₁-C₄-alkyl;

R¹² is hydroxyl, C₁-C₆-alkylsulfonyloxy, C₁-C₆-alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; particularly preferably hydroxyl;

R¹³ is C₃-C₆-cycloalkyl, C₅-C₆-cycloalkenyl or a bi or tricyclic carbocyclic ring system selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl and norbornenyl; particularly preferably C₃-C₆-cycloalkyl; with particular preference cyclopropyl.

Most preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is CR⁷R⁸;

Y is O, S or NR⁹;

R²,R³,R⁷,R⁸ are hydrogen or C₁-C₄-alkyl; preferably hydrogen, methyl or ethyl; particularly preferably hydrogen or methyl;

R⁹ is hydrogen or C₁-C₄-alkyl; preferably C₁-C₄-alkyl.

Most preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is CR⁷R⁸;

Y is O, S or NR⁹;

R²,R⁷ are hydrogen or C₁-C₄-alkyl; preferably hydrogen, methyl or ethyl; particularly preferably hydrogen or methyl;

R³ and R⁸ together form a bond;

R⁹ is hydrogen or C₁-C₄-alkyl; preferably C₁-C₄-alkyl.

Especially preferred in this case are the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where Y is S.

Particular preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is CR⁷R⁸;

Y is O, S or NR⁹;

R¹ is halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy; particularly preferably halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with particular preference chlorine, methyl or methoxy;

R²,R³,R⁷,R⁸ are hydrogen or C₁-C₄-alkyl; or R³ and R⁸ together form a bond; particularly preferably hydrogen, methyl or ethyl; or R³ and R⁸ together form a bond;

R⁴ is halogen, C₁-C₄-alkylthio or C₁-C₄-alkylsulfonyl; particularly preferably chlorine or bromine, methylthio, ethylthio or 1-methyl-1-ethylthio or methylsulfonyl, ethylsulfonyl, 1-methylethylsulfonyl or propylsulfonyl;

R⁵ is hydrogen;

R⁹ is hydrogen or C₁-C₄-alkyl; particularly preferably C₁-C₄-alkyl; with particular preference methyl or ethyl;

R¹² is hydroxyl, C₁-C₆-alkylsulfonyloxy, C₁-C₆-alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; particularly preferably hydroxyl;

R¹³ is C₃-C₆-cycloalkyl, C₅-C₆-cycloalkenyl or a bi- or tricyclic carbocyclic ring system selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl and norbornenyl; particularly preferably C₃-C₆-cycloalkyl; with particular preference cyclopropyl.

Preference is furthermore given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is CR⁷R⁸;

Y is O, S or NR⁹;

R²,R³,R⁷,R⁸ are hydrogen or C₁-C₄-alkyl; preferably hydrogen, methyl or ethyl; particularly preferably hydrogen or methyl;

R⁹ is hydrogen or C₁-C₄-alkyl; preferably C₁-C₄-alkyl.

Most preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is CR⁷R⁸;

Y is O, S or NR⁹;

R²,R⁷ are hydrogen or C₁-C₄-alkyl; preferably hydrogen, methyl or ethyl; with particular preference hydrogen or methyl;

R³ and R⁸ together form a bond;

R⁹ is hydrogen or C₁-C₄-alkyl; preferably C₁-C₄-alkyl.

Especially preferred in this case are the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where Y is S.

Preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where the variables have the following meanings:

X is O;

Y is CR¹⁰R¹¹;

R¹ is halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy; particularly preferably chlorine, methyl or methoxy; also particularly preferably halogen or C₁-C₄-alkyl; with particular preference chlorine or methyl;

R¹,R³,R¹⁰,R¹¹ are hydrogen;

R⁴ is C₁-C₄-alkylsulfonyl; particularly preferably methylsulfonyl;

R⁵ is hydrogen;

R¹² is hydroxyl, C₁-C₆-alkoxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; particularly preferably hydroxyl, C₁-C₆-alkoxy or phenylcarbonyloxy, where the phenyl radical may be partially or fully halogenated and/or may carry one to three of the following groups; nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

R¹³ is C₃-C₆-cycloalkyl or a bi- or tricyclic ring system selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl or norbornenyl; particularly preferably cyclopropyl, cyclopentyl, 2-norbornyl or 2-adamantyl; with particular preference cyclopentyl or 2-norbornyl; also with particular preference cyclopropyl;

R¹⁴ is hydrogen;

Preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where the variables have the following meanings:

X is O;

Y is CR¹⁰R¹¹;

R¹ is halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy;

R⁴ is C₁-C₄-alkylsulfonyl;

R¹³ is C₃-C₆-cycloalkyl.

Most particularly preferred are the compounds of the formula Ia1 (=I where R¹=Cl; R¹³=cyclo-C₃H₅ and R⁵ and R¹⁴=H), in particular the compounds Ia1.1 to Ta1.765 of Table 1, where the radical definitions X, Y and R¹ to R¹⁴ are of particular importance for the compounds according to the invention not only in combination with one another but also in each case on their own.

TABLE 1 No. X R² R³ Y R⁴ R¹² Ia1.1 O H H CH₂ SCH₃ OH Ia1.2 O H H CH₂ SCH₂CH₃ OH Ia1.3 O H H CH₂ SO₂CH₃ OH Ia1.4 O H H CH₂ SO₂CH₂CH₃ OH Ia1.5 O H H CH₂ SO₂CH(CH₃)₂ OH Ia1.6 O H H CH₂ SO₂(CH₂)₂CH₃ OH Ia1.7 O H H CH₃ Cl OH Ia1.8 O H H CH₂ Br OH Ia1.9 O H H CH₂ NO₂ OH Ia1.10 O H H CH₂ CHF₂ OH Ia1.11 O H H CH₂ CF₃ OH Ia1.12 O H H CH₂ OCH₃ OH Ia1.13 O H H CH₂ OCH₂CH₃ OH Ia1.14 O H H CH₂ OCHF₂ OH Ia1.15 O H H CH₂ OCF₃ OH Ia1.16 O CH₃ H CH₂ SCH₃ OH Ia1.17 O CH₃ H CH₂ SCH₂CH₃ OH Ia1.18 O CH₃ H CH₂ SO₂CH₃ OH Ia1.19 O CH₃ H CH₂ SO₂CH₂CH₃ OH Ia1.20 O CH₃ H CH₂ SO₂CH(CH₃)₂ OH Ia1.21 O CH₃ H CH₂ SO₂(CH₂)₂CH₃ OH Ia1.22 O CH₃ H CH₂ Cl OH Ia1.23 O CH₃ H CH₂ Br OH Ia1.24 O CH₃ H CH₂ NO₂ OH Ia1,25 O CH₃ H CH₂ CHF₂ OH Ia1.26 O CH₃ H CH₂ CF₃ OH Ia1.27 O CH₃ H CH₂ OCH₃ OH Ia1.28 O CH₃ H CH₂ OCH₂CH₃ OH Ia1.29 O CH₃ H CH₂ OCHF₂ OH Ia1.30 O CH₃ H CH₂ OCF₃ OH Ia1.31 O CH₃ CH₃ CH₂ SCH₃ OH Ia1.32 O CH₃ CH₃ CH₂ SCH₂CH₃ OH Ia1.33 O CH₃ CH₃ CH₂ SO₂CH₃ OH Ia1.34 O CH₃ CH₃ CH₂ SO₂CH₂CH₃ OH Ia1.35 O CH₃ CH₃ CH₂ SO₂CH(CH₃)₂ OH Ia1.36 O CH₃ CH₃ CH₂ SO₂(CH₂)₂CH₃ OH Ia1.37 O CH₃ CH₃ CH₂ Cl OH Ia1.38 O CH₃ CH₃ CH₂ Br OH Ia1.39 O CH₃ CH₃ CH₂ NO₂ OH Ia1.40 O CH₃ CH₃ CH₂ CHF₂ OH Ia1.41 O CH₃ CH₃ CH₂ CF₃ OH Ia1.42 O CH₃ CH₃ CH₂ OCH₃ OH Ia1.43 O CH₃ CH₃ CH₂ OCH₂CH₃ OH Ia1.44 O CH₃ CH₃ CH₂ OCHF₂ OH Ia1.45 O CH₃ CH₃ CH₂ OCF₃ OH Ia1.46 O CH₂Cl H CH₂ SCH₃ OH Ia1.47 O CH₂Cl H CH₂ SCH₂CH₃ OH Ia1.48 O CH₂Cl H CH₂ SO₂CH₃ OH Ia1.49 O CH₂Cl H CH₂ SO₂CH₂CH₃ OH Ia1.50 O CH₂Cl H CH₂ SO₂CH(CH₃)₂ OH Ia1.51 O CH₂Cl H CH₂ SO₂(CH₂)₂CH₃ OH Ia1.52 O CH₂Cl H CH₂ Cl OH Ia1.53 O CH₂Cl H CH₂ Br OH Ia1.54 O CH₂Cl H CH₂ NO₂ OH Ia1.55 O CH₂Cl H CH₂ CHF₂ OH Ia1.56 O CH₂Cl H CH₂ CF₃ OH Ia1.57 O CH₂Cl H CH₂ OCH₃ OH Ia1.58 O CH₂Cl H CH₂ OCH₂CH₃ OH Ia1.59 O CH₂Cl H CH₂ OCHF₂ OH Ia1.60 O CH₂Cl H CH₂ OCF₃ OH Ia1.61 O CH₂CH₃ H CH₂ SCH₃ OH Ia1.62 O CH₂CH₃ H CH₂ SCH₂CH₃ OH Ia1.63 O CH₂CH₃ H CH₂ SO₂CH₃ OH Ia1.64 O CH₂CH₃ H CH₂ SO₃CH₂CH₃ OH Ia1.65 O CH₂CH₃ H CH₂ SO₂CH(CH₃)₂ OH Ia1.66 O CH₂CH₃ H CH₂ SO₂(CH₂)₂CH₃ OH Ia1.67 O CH₂CH₃ H CH₂ Cl OH Ia1.68 O CH₂CH₃ H CH₂ Br OH Ia1.69 O CH₂CH₃ H CH₂ NO₂ OH Ia1.70 O CH₂CH₃ H CH₂ CHF₂ OH Ia1.71 O CH₂CH₃ R CH₂ CF₃ OH Ia1.72 O CH₂CH₃ H CH₂ OCH₃ OH Ia1.73 O CH₂CH₃ H CH₂ OCH₂CH₃ OH Ia1.74 O CH₂CH₃ H CH₂ OCHF₂ OH Ia1.75 O CH₂CH₃ H CH₂ OCF₃ OH Ia1.76 O CH₂CH₃ CH₂CH₃ CH₂ SCH₃ OH Ia1.77 O CH₂CH₃ CH₂CH₃ CH₂ SCH₂CH₃ OH Ia1.78 O CH₂CH₃ CH₂CH₃ CH₂ SO₂CH₃ OH Ia1.79 O CH₂CH₃ CH₂CH₃ CH₂ SO₂CH₂CH₃ OH Ia1.80 O CH₂CH₃ CH₂CH₃ CH₂ SO₂CH(CH₃)₂ OH Ia1.81 O CH₂CH₃ CH₂CH₃ CH₂ SO₂(CH₂)₂CH₃ OH Ia1.82 O CH₂CH₃ CH₂CH₃ CH₂ Cl OH Ia1.83 O CH₂CH₃ CH₂CH₃ CH₂ Br OH Ia1.84 O CH₂CH₃ CH₂CH₃ CH₂ NO₂ OH Ia1.85 O CH₂CH₃ CH₂CH₃ CH₂ CHF₂ OH Ia1.86 O CH₂CH₃ CH₂CH₃ CH₂ CF₃ OH Ia1.87 O CH₂CH₃ CH₂CH₃ CH₂ OCH₃ OH Ia1.88 O CH₂CH₃ CH₂CH₃ CH₂ OCH₂CH₃ OH Ia1.89 O CH₂CH₃ CH₂CH₃ CH₂ OCHF₂ OH Ia1.90 O CH₂CH₃ CH₂CH₃ CH₂ OCF₃ OH Ia1.91 O H H CH(CH₃) SCH₃ OH Ia1.92 O H H CH(CH₃) SCH₂CH₃ OH Ia1.93 O H H CH(CH₃) SO₂CH₃ OH Ia1.94 O H H CH(CH₃) SO₂CH₂CH₃ OH Ia1.95 O H H CH(CH₃) SO₂CH(CH₃)₂ OH Ia1.96 O H H CH(CH₃) SO₂(CH₂)₂CH₃ CH Ia1.97 O H H CH(CH₃) Cl OH Ia1.98 O H H CH(CH₃) Br OH Ia1.99 O H H CH(CH₃) NO₂ OH Ia1.100 O H H CH(CH₃) CHF₂ OH Ia1.101 O H H CH(CH₃) CF₃ OH Ia1.102 O H H CH(CH₃) OCH₃ OH Ia1.103 O H H CH(CH₃) OCH₂CH₃ OH Ia1.104 O H H CH(CH₃) OCHF₂ OH Ia1.105 O H H CH(CH₃) OCF₃ OH Ia1.106 O CH₃ H CH(CH₃) SCH₃ OH Ia1.107 O CH₃ H CH(CH₃) SCH₂CH₃ OH Ia1.108 O CH₃ H CH(CH₃) SO₂CH₃ OH Ia1.109 O CH₃ H CH(CH₃) SO₂CH₂CH₃ OH Ia1.110 O CH₂ H CH(CH₃) SO₂CH(CH₃)₂ OH Ia1.111 O CH₃ H CH(CH₃) SO₂(CH₂)₂CH₃ OH Ia1.112 O CH₃ H CH(CH₃) Cl OH Ia1.113 O CH₃ H CH(CH₃) Br OH Ia1.114 O CH₃ H CH(CH₃) NO₂ OH Ia1.115 O CH₃ H CH(CH₃) CHF₂ OH Ia1.116 O CH₃ H CH(CH₃) CF₃ OH Ia1.117 O CH₃ H CH(CH₃) OCH₃ OH Ia1.118 O CH₃ H CH(CH₃) OCH₂CH₃ OH Ia1.119 O CH₃ H CH(CH₃) OCHF₂ OH Ia1.120 O CH₃ H CH(CH₃) OCF₃ OH Ia1.121 O CH₃ CH₃ CH(CH₃) SCH₃ OH Ia1.122 O CH₃ CH₃ CH(CH₃) SCH₂CH₃ OH Ia1.123 O CH₃ CH₃ CH(CH₃) SO₂CH₃ OH Ia1.124 O CH₃ CH₃ CH(CH₃) SO₂CH₂CH₃ OH Ia1.125 O CH₃ CH₃ CH(CH₃) SO₂CH(CH₃)₂ OH Ia1.126 O CH₃ CH₃ CH(CH₃) SO₂(CH₂)₂CH₃ OH Ia1.127 O CH₃ CH₃ CH(CH₃) Cl OH Ia1.128 O CH₃ CH₃ CH(CH₃) Br OH Ia1.129 O CH₃ CH₃ CH(CH₃) NO₂ OH Ia1.130 O CH₃ CH₃ CH(CH₃) CHF₂ OH Ia1.131 O CH₃ CH₃ CH(CH₃) CF₃ OH Ia1.132 O CH₃ CH₃ CH(CH₃) OCH₃ OH Ia1.133 O CH₃ CH₃ CH(CH₃) OCH₂CH₃ OH Ia1.134 O CH₃ CH₃ CH(CH₃) OCHF₂ OH Ia1.135 O CH₃ CH₃ CH(CH₃) OCF₃ OH Ia1.136 O H H C(CH₃)₂ SCH₃ OH Ia1.137 O H H C(CH₃)₂ SCH₂CH₃ OH Ia1.138 O H H C(CH₃)₂ SO₂CH₃ OH Ia1.139 O H H C(CH₃)₂ SO₂CH₂CH₃ OH Ia1.140 O H H C(CH₃)₂ SO₂CH(CH₃)₂ OH Ia1.141 O H H C(CH₃)₂ SO₂(CH₂)₂CH₃ OH Ia1.142 O H H C(CH₃)₂ Cl OH Ia1.143 O H H C(CH₃)₂ Br OH Ia1.144 O H H C(CH₃)₂ NO₂ OH Ia1.145 O H H C(CH₃)₂ CHF₂ OH Ia1.146 O H H C(CH₃)₂ CF₃ OH Ia1.147 O H H C(CH₃)₂ OCH₃ OH Ia1.148 O H H C(CH₃)₂ OCH₂CH₃ OH Ia1.149 O H H C(CH₃)₂ OCHF₂ OH Ia1.150 O H H C(CH₃)₂ OCF₃ OH Ia1.151 O CH₃ H C(CH₃)₂ SCH₃ OH Ia1.152 O CH₃ H C(CH₃)₂ SCH₂CH₃ OH Ia1.153 O CH₃ H C(CH₃)₂ SO₂CH₃ OH Ia1.154 O CH₃ H C(CH₃)₂ SO₂CH₂CH₃ OH Ia1.155 O CH₃ H C(CH₃)₂ SO₂CH(CH₃)₂ OH Ia1.156 O CH₃ H C(CH₃)₂ SO₂(CH₂)₂CH₃ OH Ia1.157 O CH₃ H C(CH₃)₂ Cl OH Ia1.158 O CH₃ H C(CH₃)₂ Br OH Ia1.159 O CH₃ H C(CH₃)₂ NO₂ OH Ia1.160 O CH₃ H C(CH₃)₂ CHF₂ OH Ia1.161 O CH₃ H C(CH₃)₂ CF₃ OH Ia1.162 O CH₃ H C(CH₃)₂ OCH₃ OH Ia1.163 O CH₃ H C(CH₃)₂ OCH₂CH₃ OH Ia1.164 O CH₃ H C(CH₃)₂ OCHF₂ OH Ia1.165 O CH₃ H C(CH₃)₂ OCF₃ OH Ia1.166 O CH₃ CH₃ C(CH₃)₂ SCH₃ OH Ia1.167 O CH₃ CH₃ C(CH₃)₂ SCH₂CH₃ OH Ia1.168 O CH₃ CH₃ C(CH₃)₂ SO₂CH₃ OH Ia1.169 O CH₃ CH₃ C(CH₃)₂ SO₂CH₂CH₃ OH Ia1.170 O CH₃ CH₃ C(CH₃)₂ SO₂CH(CH₃)₂ OH Ia1.171 O CH₃ CH₃ C(CH₃)₂ SO₂(CH₂)₂CH₃ OH Ia1.172 O CH₃ CH₃ C(CH₃)₂ Cl OH Ia1.173 O CH₃ CH₃ C(CH₃)₂ Br OH Ia1.174 O CH₃ CH₃ C(CH₃)₂ NO₂ OH Ia1.175 O CH₃ CH₃ C(CH₃)₂ CHF₂ OH Ia1.176 O CH₃ CH₃ C(CH₃)₂ CF₃ OH Ia1.177 O CH₃ CH₃ C(CH₃)₂ OCH₃ OH Ia1.178 O CH₃ CH₃ C(CH₃)₂ OCH₂CH₃ OH Ia1.179 O CH₃ CH₃ C(CH₃)₂ OCHF₂ OH Ia1.180 O CH₃ CH₃ C(CH₃)₂ OCF₃ OH Ia1.181 NCH₃ H H CH₂ SCH₃ OH Ia1.182 NCH₃ H H CH₂ SCH₂CH₃ OH Ia1.183 NCH₃ H H CH₂ SO₂CH₃ OH Ia1.184 NCH₃ H H CH₂ SO₂CH₂CH₃ OH Ia1.185 NCH₃ H H CH₂ SO₂CH(CH₃)₂ OH Ia1.186 NCH₃ H H CH₂ SO₂(CH₂)₂CH₃ OH Ia1.187 NCH₃ H H CH₂ Cl OH Ia1.188 NCH₃ H H CH₂ Br OH Ia1.189 NCH₃ H H CH₂ NO₂ OH Ia1.190 NCH₃ H H CH₂ CHF₂ OH Ia1.191 NCH₃ H H CH₂ CF₃ OH Ia1.192 NCH₃ H H CH₂ OCH₃ OH Ia1.193 NCH₃ H H CH₂ OCH₂CH₃ OH Ia1.194 NCH₃ H H CH₂ OCHF₂ OH Ia1.195 NCH₃ H H CH₂ OCF₃ OH Ia1.196 NCH₃ CH₃ H CH₂ SCH₃ OH Ia1.197 NCH₃ CH₃ H CH₂ SCH₂CH₃ OH Ia1.198 NCH₃ CH₃ H CH₂ SO₂CH₃ OH Ia1.199 NCH₃ CH₃ H CH₂ SO₂CH₂CH₃ OH Ia1.200 NCH₃ CH₃ H CH₂ SO₂CH(CH₃)₂ OH Ia1.201 NCH₃ CH₃ H CH₂ SO₂(CH₂)₂CH₃ OH Ia1.202 NCH₃ CH₃ H CH₂ Cl OH Ia1.203 NCH₃ CH₃ H CH₂ Br OH Ia1.204 NCH₃ CH₃ H CH₂ NO₂ OH Ia1.205 NCH₃ CH₃ H CH₂ CHF₂ OH Ia1.206 NCH₃ CH₃ H CH₂ CF₃ OH Ia1.207 NCH₃ CH₃ H CH₂ OCH₃ OH Ia1.208 NCH₃ CH₃ H CH₂ OCH₂CH₃ OH Ia1.209 NCH₃ CH₃ H CH₂ OCHF₂ OH Ia1.210 NCH₃ CH₃ H CH₂ OCF₃ OH Ia1.211 NCH₃ CH₃ CH₃ CH₂ SCH₃ OH Ia1.212 NCH₃ CH₃ CH₃ CH₂ SCH₂CH₃ OH Ia1.213 NCH₃ CH₃ CH₃ CH₂ SO₂CH₃ OH Ia1.214 NCH₃ CH₃ CH₃ CH₂ SO₂CH₂CH₃ OH Ia1.215 NCH₃ CH₃ CH₃ CH₂ SO₂CH(CH₃)₂ OH Ia1.216 NCH₃ CH₃ CH₃ CH₂ SO₂(CH₂)₂CH₃ OH Ia1.217 NCH₃ CH₃ CH₃ CH₂ Cl OH Ia1.218 NCH₃ CH₃ CH₃ CH₂ Br OH Ia1.219 NCH₃ CH₃ CH₃ CH₂ NO₂ OH Ia1.220 NCH₃ CH₃ CH₃ CH₂ CHF₂ OH Ia1.221 NCH₃ CH₃ CH₃ CH₂ CF₃ OH Ia1.222 NCH₃ CH₃ CH₃ CH₂ OCH₃ OH Ia1.223 NCH₃ CH₃ CH₃ CH₂ OCH₂CH₃ OH Ia1.224 NCH₃ CH₃ CH₃ CH₂ OCHF₂ OH Ia1.225 NCH₃ CH₃ CH₃ CH₂ OCF₃ OH Ia1.226 NCH₃ CH₂Cl H CH₂ SCH₃ OH Ia1.227 NCH₃ CH₂Cl H CH₂ SCH₂CH₃ OH Ia1.228 NCH₃ CH₂Cl H CH₂ SO₂CH₃ OH Ia1.229 NCH₃ CH₂Cl H CH₂ SO₂CH₂CH₃ OH Ia1.230 NCH₃ CH₂Cl H CH₂ SO₂CH(CH₃)₂ OH Ia1.231 NCH₃ CH₂Cl H CH₂ SO₂(CH₂)₂CH₃ OH Ia1.232 NCH₃ CH₂Cl H CH₂ Cl OH Ia1.233 NCH₃ CH₂Cl H CH₂ Br OH Ia1.234 NCH₃ CH₂Cl H CH₂ NO₂ OH Ia1.235 NCH₃ CH₂Cl H CH₂ CHF₂ OH Ia1.236 NCH₃ CH₂Cl H CH₂ CF₃ OH Ia1.237 NCH₃ CH₂Cl H CH₂ OCH₃ OH Ia1.238 NCH₃ CH₂Cl H CH₂ OCH₂CH₃ OH Ia1.239 NCH₃ CH₂Cl H CH₂ OCHF₂ OH Ia1.240 NCH₃ CH₂Cl H CH₂ OCF₃ OH Ia1.241 NCH₃ CH₂CH₃ H CH₂ SCH₃ OH Ia1.242 NCH₃ CH₂CH₃ H CH₂ SCH₂CH₃ OH Ia1.243 NCH₃ CH₂CH₃ H CH₂ SO₂CH₃ OH Ia1.244 NCH₃ CH₂CH₃ H CH₂ SO₂CH₂CH₃ OH Ia1.245 NCH₃ CH₂CH₃ H CH₂ SO₂CH(CH₃)₂ OH Ia1.246 NCH₃ CH₂CH₃ H CH₂ SO₂(CH₂)₂CH₃ OH Ia1.247 NCH₃ CH₂CH₃ H CH₂ Cl OH Ia1.248 NCH₃ CH₂CH₃ H CH₂ Br OH Ia1.249 NCH₃ CH₂CH₃ H CH₂ NO₂ OH Ia1.250 NCH₃ CH₂CH₃ H CH₂ CHF₂ OH Ia1.251 NCH₃ CH₂CH₃ H CH₂ CF₃ OH Ia1.252 NCH₃ CH₂CH₃ H CH₂ OCH₃ OH Ia1.253 NCH₃ CH₂CH₃ H CH₂ OCH₂CH₃ OH Ia1.254 NCH₃ CH₂CH₃ H CH₂ OCHF₂ OH Ia1.255 NCH₃ CH₂CH₃ H CH₂ OCF₃ OH Ia1.256 NCH₃ CH₂CH₃ CH₂CH₃ CH₂ SCH₃ OH Ia1.257 NCH₃ CH₂CH₃ CH₂CH₃ CH₂ SCH₂CH₃ OH Ia1.258 NCH₃ CH₂CH₃ CH₂CH₃ CH₂ SO₂CH₃ OH Ia1.259 NCH₃ CH₂CH₃ CH₂CH₃ CH₂ SO₂CH₂CH₃ OH Ia1.260 NCH₃ CH₂CH₃ CH₂CH₃ CH₂ SO₂CH(CH₃)₂ OH Ia1.261 NCH₃ CH₂CH₃ CH₂CH₃ CH₂ SO₂(CH₂)₂CH₃ OH Ia1.262 NCH₃ CH₂CH₃ CH₂CH₃ CH₂ Cl OH Ia1.263 NCH₃ CH₂CH₃ CH₂CH₃ CH₂ Br OH Ia1.264 NCH₃ CH₂CH₃ CH₂CH₃ CH₂ NO₂ OH Ia1.265 NCH₃ CH₂CH₃ CH₂CH₃ CH₂ CHF₂ OH Ia1.266 NCH₃ CH₂CH₃ CH₂CH₃ CH₂ CF₃ OH Ia1.267 NCH₃ CH₂CH₃ CH₂CH₃ CH₂ OCH₃ OH Ia1.268 NCH₃ CH₂CH₃ CH₂CH₃ CH₂ OCH₂CH₃ OH Ia1.269 NCH₃ CH₂CH₃ CH₂CH₃ CH₂ OCHF₂ OH Ia1.270 NCH₃ CH₂CH₃ CH₂CH₃ CH₂ OCF₃ OH Ia1.271 NCH₃ H H CH(CH₃) SCH₃ OH Ia1.272 NCH₃ H H CH(CH₃) SCH₂CH₃ OH Ia1.273 NCH₃ H H CH(CH₃) SO₂CH₃ OH Ia1.274 NCH₃ H H CH(CH₃) SO₂CH₂CH₃ OH Ia1.275 NCH₃ H H CH(CH₃) SO₂CH(CH₃)₂ OH Ia1.276 NCH₃ H H CH(CH₃) SO₂(CH₂)₂CH₃ OH Ia1.277 NCH₃ H H CH(CH₃) Cl OH Ia1.278 NCH₃ H H CH(CH₃) Br OH Ia1.279 NCH₃ H H CH(CH₃) NO₂ OH Ia1.280 NCH₃ H H CH(CH₃) CHF₂ OH Ia1.281 NCH₃ H H CH(CH₃) CF₃ OH Ia1.282 NCH₃ H H CH(CH₃) OCH₃ OH Ia1.283 NCH₃ H H CH(CH₃) OCH₂CH₃ OH Ia1.284 NCH₃ H H CH(CH₃) OCHF₂ OH Ia1.285 NCH₃ H H CH(CH₃) OCF₃ OH Ia1.286 NCH₃ CH₃ H CH(CH₃) SCH₃ OH Ia1.287 NCH₃ CH₃ H CH(CH₃) SCH₂CH₃ OH Ia1.288 NCH₃ CH₃ H CH(CH₃) SO₂CH₃ OH Ia1.289 NCH₃ CH₃ H CH(CH₃) SO₂CH₂CH₃ OH Ia1.290 NCH₃ CH₃ H CH(CH₃) SO₂CH(CH₃)₂ OH Ia1.291 NCH₃ CH₃ H CH(CH₃) SO₂(CH₂)₂CH₃ OH Ia1.292 NCH₃ CH₃ H CH(CH₃) Cl OH Ia1.293 NCH₃ CH₃ H CH(CH₃) Br OH Ia1.294 NCH₃ CH₃ H CH(CH₃) NO₂ OH Ia1.295 NCH₃ CH₃ H CH(CH₃) CHF₂ OH Ia1.296 NCH₃ CH₃ H CH(CH₃) CF₃ OH Ia1.297 NCH₃ CH₃ H CH(CH₃) OCH₃ OH Ia1.298 NCH₃ CH₃ H CH(CH₃) OCH₂CH₃ OH Ia1.299 NCH₃ CH₃ H CH(CH₃) OCHF₂ OH Ia1.300 NCH₃ CH₃ H CH(CH₃) OCF₃ OH Ia1.301 NCH₃ CH₃ CH₃ CH(CH₃) SCH₃ OH Ia1.302 NCH₃ CH₃ CH₃ CH(CH₃) SCH₂CH₃ OH Ia1.303 NCH₃ CH₃ CH₃ CH(CH₃) SO₂CH₃ OH Ia1.304 NCH₃ CH₃ CH₃ CH(CH₃) SO₂CH₂CH₃ OH Ia1.305 NCH₃ CH₃ CH₃ CH(CH₃) SO₂CH(CH₃)₂ OH Ia1.306 NCH₃ CH₃ CH₃ CH(CH₃) SO₂(CH₂)₂H₃ OH Ia1.307 NCH₃ CH₃ CH₃ CH(CH₃) Cl OH Ia1.308 NCH₃ CH₃ CH₃ CH(CH₃) Br OH Ia1.309 NCH₃ CH₃ CH₃ CH(CH₃) NO₂ OH Ia1.310 NCH₃ CH₃ CH₃ CH(CH₃) CHF₂ OH Ia1.311 NCH₃ CH₃ CH₃ CH(CH₃) CF₃ OH Ia1.312 NCH₃ CH₃ CH₃ CH(CH₃) OCH₃ OH Ia1.313 NCH₃ CH₃ CH₃ CH(CH₃) OCH₂CH₃ OH Ia1.314 NCH₃ CH₃ CH₃ CH(CH₃) OCHF₂ OH Ia1.315 NCH₃ CH₃ CH₃ CH(CH₃) OCF₃ OH Ia1.316 NCH₃ H H C(CH₃)₂ SCH₃ OH Ia1.317 NCH₃ H H C(CH₃)₂ SCH₂CH₃ OH Ia1.318 NCH₃ H H C(CH₃)₂ SO₂CH₃ OH Ia1.319 NCH₃ H H C(CH₃)₂ SO₂CH₂CH₃ OH Ia1.320 NCH₃ H H C(CH₃)₂ SO₂CH(CH₃)₂ OH Ia1.321 NCH₃ H H C(CH₃)₂ SO₂(CH₂)₂CH₃ OH Ia1.322 NCH₃ H H C(CH₃)₂ Cl OH Ia1.323 NCH₃ H H C(CH₃)₂ Br OH Ia1.324 NCH₃ H H C(CH₃)₂ NO₂ OH Ia1.325 NCH₃ H H C(CH₃)₂ CHF₂ OH Ia1.326 NCH₃ H H C(CH₃)₂ CF₃ OH Ia1.327 NCH₃ H H C(CH₃)₂ OCH₃ OH Ia1.328 NCH₃ H H C(CH₃)₂ OCH₂CH₃ OH Ia1.329 NCH₃ H H C(CH₃)₂ OCHF₂ OH Ia1.330 NCH₃ H H C(CH₃)₂ OCF₃ OH Ia1.331 NCH₃ CH₃ H C(CH₃)₂ SCH₃ OH Ia1.332 NCH₃ CH₃ H C(CH₃)₂ SCH₂CH₃ OH Ia1.333 NCH₃ CH₃ H C(CH₃)₂ SO₂CH₃ OH Ia1.334 NCH₃ CH₃ H C(CH₃)₂ SO₂CH₂CH₃ OH Ia1.335 NCH₃ CH₃ H C(CH₃)₂ SO₂CH(CH₃)₂ OH Ia1.336 NCH₃ CH₃ H C(CH₃)₂ SO₂(CH₂)₂CH₃ OH Ia1.337 NCH₃ CH₃ H C(CH₃)₂ Cl OH Ia1.338 NCH₃ CH₃ H C(CH₃)₂ Br OH Ia1.339 NCH₃ CH₃ H C(CH₃)₂ NO₂ OH Ia1.340 NCH₃ CH₃ H C(CH₃)₂ CHF₂ OH Ia1.341 NCH₃ CH₃ H C(CH₃)₂ CF₃ OH Ia1.342 NCH₃ CH₃ H C(CH₃)₂ OCH₃ OH Ia1.343 NCH₃ CH₃ H C(CH₃)₂ OCH₂CH₃ OH Ia1.344 NCH₃ CH₃ H C(CH₃)₂ OCHF₂ OH Ia1.345 NCH₃ CH₃ H C(CH₃)₂ OCF₃ OH Ia1.346 NCH₃ CH₃ CH₃ C(CH₃)₂ SCH₃ OH Ia1.347 NCH₃ CH₃ CH₃ C(CH₃)₂ SCH₂CH₃ OH Ia1.348 NCH₃ CH₃ CH₃ C(CH₃)₂ SO₂CH₃ OH Ia1.349 NCH₃ CH₃ CH₃ C(CH₃)₂ SO₂CH₂CH₃ OH Ia1.350 NCH₃ CH₃ CH₃ C(CH₃)₂ SO₂CH(CH₃)₂ OH Ia1.351 NCH₃ CH₃ CH₃ C(CH₃)₂ SO₂(CH₂)₂CH₃ OH Ia1.352 NCH₃ CH₃ CH₃ C(CH₃)₂ Cl OH Ia1.353 NCH₃ CH₃ CH₃ C(CH₃)₂ Br OH Ia1.354 NCH₃ CH₃ CH₃ C(CH₃)₂ NO₂ OH Ia1.355 NCH₃ CH₃ CH₃ C(CH₃)₂ CHF₂ OH Ia1.356 NCH₃ CH₃ CH₃ C(CH₃)₂ CF₃ OH Ia1.357 NCH₃ CH₃ CH₃ C(CH₃)₂ OCH₃ OH Ia1.358 NCH₃ CH₃ CH₃ C(CH₃)₂ OCH₂CH₃ OH Ia1.359 NCH₃ CH₃ CH₃ C(CH₃)₂ OCHF₂ OH Ia1.360 NCH₃ CH₃ CH₃ C(CH₃)₂ OCF₃ OH Ia1.361 CH₂ H H O SCH₃ OH Ia1.362 CH₂ H H O SCH₂CH₃ OH Ia1.363 CH₂ H H O SO₂CH₃ OH Ia1.364 CH₂ H H O SO₂CH₂CH₃ OH Ia1.365 CH₂ H H O SO₂CH(CH₃)₂ OH Ia1.366 CH₂ H H O SO₂(CH₂)₂CH₃ OH Ia1.367 CH₂ H H O Cl OH Ia1.368 CH₂ H H O Br OH Ia1.369 CH₂ H H O NO₂ OH Ia1.370 CH₂ H H O CHF₂ OH Ia1.371 CH₂ H H O CF₃ OH Ia1.372 CH₂ H H O OCH₃ OH Ia1.373 CH₂ H H O OCH₂CH₃ OH Ia1.374 CH₂ H H O OCHF₂ OH Ia1.375 CH₂ H H O OCF₃ OH Ia1.376 CH₂ CH₃ H O SCH₃ OH Ia1.377 CH₂ CH₃ H O SCH₂CH₃ OH Ia1.378 CH₂ CH₃ H O SO₂CH₃ OH Ia1.379 CH₂ CH₃ H O SO₂CH₂CH₃ OH Ia1.380 CH₂ CH₃ H O SO₂CH(CH₃)₂ OH Ia1.381 CH₂ CH₃ H O SO₂(CH₂)₂CH₃ OH Ia1.382 CH₂ CH₃ H O Cl OH Ia1.383 CH₂ CH₃ H O Br OH Ia1.384 CH₂ CH₃ H O NO₂ OH Ia1.385 CH₂ CH₃ H O CHF₂ OH Ia1.386 CH₂ CH₃ H O CF₃ OH Ia1.387 CH₂ CH₃ H O OCH₃ OH Ia1.388 CH₂ CH₃ H O OCH₂CH₃ OH Ia1.389 CH₂ CH₃ H O OCHF₂ OH Ia1.390 CH₂ CH₃ H O OCF₃ OH Ia1.391 CH₂ CH₃ CH₃ O SCH₃ OH Ia1.392 CH₂ CH₃ CH₃ O SCH₂CH₃ OH Ia1.393 CH₂ CH₃ CH₃ O SO₂CH₃ OH Ia1.394 CH₂ CH₃ CH₃ O SO₂CH₂CH₃ OH Ia1.395 CH₂ CH₃ CH₃ O SO₂CH(CH₃)₂ OH Ia1.396 CH₂ CH₃ CH₃ O SO₂(CH₂)₂CH₃ OH Ia1.397 CH₂ CH₃ CH₃ O Cl OH Ia1.398 CH₂ CH₃ CH₃ O Br OH Ia1.399 CH₂ CH₃ CH₃ O NO₂ OH Ia1.400 CH₂ CH₃ CH₃ O CHF₂ OH Ia1.401 CH₂ CH₃ CH₃ O CF₃ OH Ia1.402 CH₂ CH₃ CH₃ O OCH₃ OH Ia1.403 CH₂ CH₃ CH₃ O OCH₂CH₃ OH Ia1.404 CH₂ CH₃ CH₃ O OCHF₂ OH Ia1.405 CH₂ CH₃ CH₃ O OCF₃ OH Ia1.406 CH₂ H H S SCH₃ OH Ia1.407 CH₂ H H S SCH₂CH₃ OH Ia1.408 CH₂ H H S SO₂CH₃ OH Ia1.409 CH₂ H H S SO₂CH₂CH₃ OH Ia1.410 CH₂ H H S SO₂CH(CH₃)₂ OH Ia1.411 CH₂ H H S SO₂(CH₂)₂CH₃ OH Ia1.412 CH₂ H H S Cl OH Ia1.413 CH₂ H H S Br OH Ia1.414 CH₂ H H S NO₃ OH Ia1.415 CH₂ H H S CHF₂ OH Ia1.416 CH₂ H H S CF₃ OH Ia1.417 CH₂ H H S OCH₃ OH Ia1.418 CH₂ H H S OCH₂CH₃ OH Ia1.419 CH₂ H H S OCHF₂ OH Ia1.420 CH₂ H H S OCF₃ OH Ia1.421 CH₂ CH₃ H S SCH₃ OH Ia1.422 CH₂ CH₃ H S SCH₂CH₃ OH Ia1.423 CH₂ CH₃ H S SO₂CH₃ OH Ia1.424 CH₂ CH₃ H S SO₂CH₂CH₃ OH Ia1.425 CH₂ CH₃ H S SO₂CH(CH₃)₂ OH Ia1.426 CH₂ CH₃ H S SO₂(CH₂)₂CH₃ OH Ia1.427 CH₂ CH₃ H S Cl OH Ia1.428 CH₂ CH₃ H S Br OH Ia1.429 CH₂ CH₃ H S NO₂ OH Ia1.430 CH₂ CH₃ H S CHF₂ OH Ia1.431 CH₂ CH₃ H S CF₃ OH Ia1.432 CH₂ CH₃ H S OCH₃ OH Ia1.433 CH₂ CH₃ H S OCH₂CH₃ OH Ia1.434 CH₂ CH₃ H S OCHF₂ OH Ia1.435 CH₂ CH₃ H S OCF₃ OH Ia1.436 CH₂ CH₃ CH₃ S SCH₃ OH Ia1.437 CH₂ CH₃ CH₃ S SCH₂CH₃ OH Ia1.438 CH₂ CH₃ CH₃ S SO₂CH₃ OH Ia1.439 CH₂ CH₃ CH₃ S SO₂CH₂CH₃ OH Ia1.440 CH₂ CH₃ CH₃ S SO₂CH(CH₃)₂ OH Ia1.441 CH₂ CH₃ CH₃ S SO₂(CH₂)₂CH₃ OH Ia1.442 CH₂ CH₃ CH₃ S Cl OH Ia1.443 CH₂ CH₃ CH₃ S Br OH Ia1.444 CH₂ CH₃ CH₃ S NO₂ OH Ia1.445 CH₂ CH₃ CH₃ S CHF₂ OH Ia1.446 CH₂ CH₃ CH₃ S CF₃ OH Ia1.447 CH₂ CH₃ CH₃ S OCH₃ OH Ia1.448 CH₂ CH₃ CH₃ S OCH₂CH₃ OH Ia1.449 CH₂ CH₃ CH₃ S OCHF₂ OH Ia1.450 CH₂ CH₃ CH₃ S OCF₃ OH Ia1.451 CH₂ H H NCH₃ SCH₃ OH Ia1.452 CH₂ H H NCH₃ SCH₂CH₃ OH Ia1.453 CH₂ H H NCH₃ SO₂CH₃ OH Ia1.454 CH₂ H H NCH₃ SO₂CH₂CH₃ OH Ia1.455 CH₂ H H NCH₃ SO₂CH(CH₃)₂ OH Ia1.456 CH₂ H H NCH₃ SO₂(CH₂)₂CH₃ OH Ia1.457 CH₂ H H NCH₃ Cl OH Ia1.458 CH₂ H H NCH₃ Br OH Ia1.459 CH₂ H H NCH₃ NO₂ OH Ia1.460 CH₂ H H NCH₃ CHF₂ OH Ia1.461 CH₂ H H NCH₃ CF₃ OH Ia1.462 CH₂ H H NCH₃ OCH₃ OH Ia1.463 CH₂ H H NCH₃ OCH₂CH₃ OH Ia1.464 CH₂ H H NCH₃ OCHF₂ OH Ia1.465 CH₂ H H NCH₃ OCF₃ OH Ia1.466 CH₂ CH₃ H NCH₃ SCH₃ OH Ia1.467 CH₂ CH₃ H NCH₃ SCH₂CH₃ OH Ia1.468 CH₂ CH₃ H NCH₃ SO₂CH₃ OH Ia1.469 CH₂ CH₃ H NCH₃ SO₂CH₂CH₃ OH Ia1.470 CH₂ CH₃ H NCH₃ SO₂CH(CH₃)₂ OH Ia1.471 CH₂ CH₃ H NCH₃ SO₂(CH₂)₂CH₃ OH Ia1.472 CH₂ CH₃ H NCH₃ Cl OH Ia1.473 CH₂ CH₃ H NCH₃ Br OH Ia1.474 CH₂ CH₃ H NCH₃ NO₂ OH Ia1.475 CH₂ CH₃ H NCH₃ CHF₂ OH Ia1.476 CH₂ CH₃ H NCH₃ CF₃ OH Ia1.477 CH₂ CH₃ H NCH₃ OCH₃ OH Ia1.478 CH₂ CH₃ H NCH₃ OCH₂CH₃ OH Ia1.479 CH₂ CH₃ H NCH₃ OCHF₂ OH Ia1.480 CH₂ CH₃ H NCH₃ OCF₃ OH Ia1.481 CH₂ CH₃ CH₃ NCH₃ SCH₃ OH Ia1.482 CH₂ CH₃ CH₃ NCH₃ SCH₂CH₃ OH Ia1.483 CH₂ CH₃ CH₃ NCH₃ SO₂CH₃ OH Ia1.484 CH₂ CH₃ CH₃ NCH₃ SO₂CH₂CH₃ OH Ia1.485 CH₂ CH₃ CH₃ NCH₃ SO₂CH(CH₃)₂ OH Ia1.486 CH₂ CH₃ CH₃ NCH₃ SO₂(CH₂)₂CH₃ OH Ia1.487 CH₂ CH₃ CH₃ NCH₃ Cl OH Ia1.488 CH₂ CH₃ CH₃ NCH₃ Br OH Ia1.489 CH₂ CH₃ CH₃ NCH₃ NO₂ OH Ia1.490 CH₂ CH₃ CH₃ NCH₃ CHF₂ OH Ia1.491 CH₂ CH₃ CH₃ NCH₃ CF₃ OH Ia1.492 CH₂ CH₃ CH₃ NCH₃ OCH₃ OH Ia1.493 CH₂ CH₃ CH₃ NCH₃ OCH₂CH₃ OH Ia1.494 CH₂ CH₃ CH₃ NCH₃ OCHF₂ OH Ia1.495 CH₂ CH₃ CH₃ NCH₃ OCF₃ OH Ia1.496 CHCH₃ H H O SCH₃ OH Ia1.497 CHCH₃ H H O SCH₂CH₃ OH Ia1.498 CHCH₃ H H O SO₂CH₃ OH Ia1.499 CHCH₃ H H O SO₂CH₂CH₃ OH Ia1.500 CHCH₃ H H O SO₂CH(CH₃)₂ OH Ia1.501 CHCH₃ H H O SO₂(CH₂)₂CH₃ OH Ia1.502 CHCH₃ H H O Cl OH Ia1.503 CHCH₃ H H O Br OH Ia1.504 CHCH₃ H H O NO₂ OH Ia1.505 CHCH₃ H H O CHF₂ OH Ia1.506 CHCH₃ H H O CF₃ OH Ia1.507 CHCH₃ H H O OCH₃ OH Ia1.508 CHCH₃ H H O OCH₂CH₃ OH Ia1.509 CHCH₃ H H O OCHF₂ OH Ia1.510 CHCH₃ H H O OCF₃ OH Ia1.511 CHCH₃ CH₃ H O SCH₃ OH Ia1.512 CHCH₃ CH₃ H O SCH₂CH₃ OH Ia1.513 CHCH₃ CH₃ H O SO₂CH₃ OH Ia1.514 CHCH₃ CH₃ H O SO₂CH₂CH₃ OH Ia1.515 CHCH₃ CH₃ H O SO₂CH(CH₃)₂ OH Ia1.516 CHCH₃ CH₃ H O SO₂(CH₂)₂CH₃ OH Ia1.517 CHCH₃ CH₃ H O Cl OH Ia1.518 CHCH₃ CH₃ H O Br OH Ia1.519 CHCH₃ CH₃ H O NO₂ OH Ia1.520 CHCH₃ CH₃ H O CHF₂ OH Ia1.521 CHCH₃ CH₃ H O CF₃ OH Ia1.522 CHCH₃ CH₃ H O OCH₃ OH Ia1.523 CHCH₃ CH₃ H O OCH₂CH₃ OH Ia1.524 CHCH₃ CH₃ H O OCHF₂ OH Ia1.525 CHCH₃ CH₃ H O OCF₃ OH Ia1.526 CHCH₃ CH₃ CH₃ O SCH₃ OH Ia1.527 CHCH₃ CH₃ CH₃ O SCH₂CH₃ OH Ia1.528 CHCH₃ CH₃ CH₃ O SO₂CH₃ OH Ia1.529 CHCH₃ CH₃ CH₃ O SO₂CH₂CH₃ OH Ia1.530 CHCH₃ CH₃ CH₃ O SO₂CH(CH₃)₂ OH Ia1.531 CHCH₃ CH₃ CH₃ O SO₂(CH₂)₂CH₃ OH Ia1.532 CHCH₃ CH₃ CH₃ O Cl OH Ia1.533 CHCH₃ CH₃ CH₃ O Br OH Ia1.534 CHCH₃ CH₃ CH₃ O NO₂ OH Ia1.535 CHCH₃ CH₃ CH₃ O CHF₂ OH Ia1.536 CHCH₃ CH₃ CH₃ O CF₃ OH Ia1.537 CHCH₃ CH₃ CH₃ O OCH₃ OH Ia1.538 CHCH₃ CH₃ CH₃ O OCH₂CH₃ OH Ia1.539 CHCH₃ CH₃ CH₃ O OCHF₂ OH Ia1.540 CHCH₃ CH₃ CH₃ O OCF₃ OH Ia1.541 CHCH₃ H H S SCH₃ OH Ia1.542 CHCH₃ H H S SCH₂CH₃ OH Ia1.543 CHCH₃ H H S SO₂CH₃ OH Ia1.544 CHCH₃ H H S SO₂CH₂CH₃ OH Ia1.545 CHCH₃ H H S SO₂CH(CH₃)₂ OH Ia1.546 CHCH₃ H H S SO₂(CH₂)₂CH₃ OH Ia1.547 CHCH₃ H H S Cl OH Ia1.548 CHCH₃ H H S Br OH Ia1.549 CHCH₃ H H S NO₂ OH Ia1.550 CHCH₃ H H S CHF₂ OH Ia1.551 CHCH₃ H H S CF₃ OH Ia1.552 CHCH₃ H H S OCH₃ OH Ia1.553 CHCH₃ H H S OCH₂CH₃ OH Ia1.554 CHCH₃ H H S OCHF₂ OH Ia1.555 CHCH₃ H H S OCF₃ OH Ia1.556 CHCH₃ CH₃ H S SCH₃ OH Ia1.557 CHCH₃ CH₃ H S SCH₂CH₃ OH Ia1.558 CHCH₃ CH₃ H S SO₂CH₃ OH Ia1.559 CHCH₃ CH₃ H S SO₂CH₂CH₃ OH Ia1.560 CHCH₃ CH₃ H S SO₂CH(CH₃)₂ OH Ia1.561 CHCH₃ CH₃ H S SO₂(CH₂)₂CH₃ OH Ia1.562 CHCH₃ CH₃ H S Cl OH Ia1.563 CHCH₃ CH₃ H S Br OH Ia1.564 CHCH₃ CH₃ H S NO₂ OH Ia1.565 CHCH₃ CH₃ H S CHF₂ OH Ia1.566 CHCH₃ CH₃ H S CF₃ OH Ia1.567 CHCH₃ CH₃ H S OCH₃ OH Ia1.568 CHCH₃ CH₃ H S OCH₂CH₃ OH Ia1.569 CHCH₃ CH₃ H S OCHF₂ OH Ia1.570 CHCH₃ CH₃ H S OCF₃ OH Ia1.571 CHCH₃ CH₃ CH₃ S SCH₃ OH Ia1.572 CHCH₃ CH₃ CH₃ S SCH₂CH₃ OH Ia1.573 CHCH₃ CH₃ CH₃ S SO₂CH₃ OH Ia1.574 CHCH₃ CH₃ CH₃ S SO₂CH₂CH₃ OH Ia1.575 CHCH₃ CH₃ CH₃ S SO₂CH(CH₃)₂ OH Ia1.576 CHCH₃ CH₃ CH₃ S SO₂(CH₂)₂CH₃ OH Ia1.577 CHCH₃ CH₃ CH₃ S Cl OH Ia1.578 CHCH₃ CH₃ CH₃ S Br OH Ia1.579 CHCH₃ CH₃ CH₃ S NO₂ OH Ia1.580 CHCH₃ CH₃ CH₃ S CHF₂ OH Ia1.581 CHCH₃ CH₃ CH₃ S CF₃ OH Ia1.582 CHCH₃ CH₃ CH₃ S OCH₃ OH Ia1.583 CHCH₃ CH₃ CH₃ S OCH₂CH₃ OH Ia1.584 CHCH₃ CH₃ CH₃ S OCHF₂ OH Ia1.585 CHCH₃ CH₃ CH₃ S OCF₃ OH Ia1.586 CHCH₃ H H NCH₃ SCH₃ OH Ia1.587 CHCH₃ H H NCH₃ SCH₂CH₃ OH Ia1.588 CHCH₃ H H NCH₃ SO₂CH₃ OH Ia1.589 CHCH₃ H H NCH₃ SO₂CH₂CH₃ OH Ia1.590 CHCH₃ H H NCH₃ SO₂CH(CH₃)₂ OH Ia1.591 CHCH₃ H H NCH₃ SO₂(CH₂)₂CH₃ OH Ia1.592 CHCH₃ H H NCH₃ Cl OH Ia1.593 CHCH₃ H H NCH₃ Br OH Ia1.594 CHCH₃ H H NCH₃ NO₂ OH Ia1.595 CHCH₃ H H NCH₃ CHF₂ OH Ia1.596 CHCH₃ H H NCH₃ CF₃ OH Ia1.597 CHCH₃ H H NCH₃ OCH₃ OH Ia1.598 CHCH₃ H H NCH₃ OCH₂CH₃ OH Ia1.599 CHCH₃ H H NCH₃ OCHF₂ OH Ia1.600 CHCH₃ H H NCH₃ OCF₃ OH Ia1.601 CHCH₃ CH₃ H NCH₃ SCH₃ OH Ia1.602 CHCH₃ CH₃ H NCH₃ SCH₂CH₃ OH Ia1.603 CHCH₃ CH₃ H NCH₃ SO₂CH₃ OH Ia1.604 CHCH₃ CH₃ H NCH₃ SO₂CH₂CH₃ OH Ia1.605 CHCH₃ CH₃ H NCH₃ SO₂CH(CH₃)₂ OH Ia1.606 CHCH₃ CH₃ H NCH₃ SO₂(CH₂)₂CH₃ OH Ia1.607 CHCH₃ CH₃ H NCH₃ Cl OH Ia1.608 CHCH₃ CH₃ H NCH₃ Br OH Ia1.609 CHCH₃ CH₃ H NCH₃ NO₂ OH Ia1.610 CHCH₃ CH₃ H NCH₃ CHF₂ OH Ia1.611 CHCH₃ CH₃ H NCH₃ CF₃ OH Ia1.612 CHCH₃ CH₃ H NCH₃ OCH₃ OH Ia1.613 CHCH₃ CH₃ H NCH₃ OCH₂CH₃ OH Ia1.614 CHCH₃ CH₃ H NCH₃ OCHF₂ OH Ia1.615 CHCH₃ CH₃ H NCH₃ OCF₃ OH Ia1.616 CHCH₃ CH₃ CH₃ NCH₃ SCH₃ OH Ia1.617 CHCH₃ CH₃ CH₃ NCH₃ SCH₂CH₃ OH Ia1.618 CHCH₃ CH₃ CH₃ NCH₃ SO₂CH₃ OH Ia1.619 CHCH₃ CH₃ CH₃ NCH₃ SO₂CH₂CH₃ OH Ia1.620 CHCH₃ CH₃ CH₃ NCH₃ SO₂CH(CH₃)₂ OH Ia1.621 CHCH₃ CH₃ CH₃ NCH₃ SO₂(CH₂)₂CH₃ OH Ia1.622 CHCH₃ CH₃ CH₃ NCH₃ Cl OH Ia1.623 CHCH₃ CH₃ CH₃ NCH₃ Br OH Ia1.624 CHCH₃ CH₃ CH₃ NCH₃ NO₂ OH Ia1.625 CHCH₃ CH₃ CH₃ NCH₃ CHF₂ OH Ia1.626 CHCH₃ CH₃ CH₃ NCH₃ CF₃ OH Ia1.627 CHCH₃ CH₃ CH₃ NCH₃ OCH₃ OH Ia1.628 CHCH₃ CH₃ CH₃ NCH₃ OCH₂CH₃ OH Ia1.629 CHCH₃ CH₃ CH₃ NCH₃ OCHF₂ OH Ia1.630 CHCH₃ CH₃ CH₃ NCH₃ OCF₃ OH Ia1.631 C(CH₃)₂ H H O SCH₃ OH Ia1.632 C(CH₃)₂ H H O SCH₂CH₃ OH Ia1.633 C(CH₃)₂ H H O SO₂CH₃ OH Ia1.634 C(CH₃)₂ H H O SO₂CH₂CH₃ OH Ia1.635 C(CH₃)₂ H H O SO₂CH(CH₃)₂ OH Ia1.636 C(CH₃)₂ H H O SO₂(CH₂)₂CH₃ OH Ia1.637 C(CH₃)₂ H H O Cl OH Ia1.638 C(CH₃)₂ H H O Br OH Ia1.639 C(CH₃)₂ H H O NO₂ OH Ia1.640 C(CH₃)₂ H H O CHF₂ OH Ia1.641 C(CH₃)₂ H H O CF₃ OH Ia1.642 C(CH₃)₂ H H O OCH₃ OH Ia1.643 C(CH₃)₂ H H O OCH₂CH₃ OH Ia1.644 C(CH₃)₂ H H O OCHF₂ OH Ia1.645 C(CH₃)₂ H H O OCF₃ OH Ia1.646 C(CH₃)₂ CH₃ H O SCH₃ OH Ia1.647 C(CH₃)₂ CH₃ H O SCH₂CH₃ OH Ia1.648 C(CH₃)₂ CH₃ H O SO₂CH₃ OH Ia1.649 C(CH₃)₂ CH₃ H O SO₂CH₂CH₃ OH Ia1.650 C(CH₃)₂ CH₃ H O SO₂CH(CH₃)₂ OH Ia1.651 C(CH₃)₂ CH₃ H O SO₂(CH₂)₂CH₃ OH Ia1.652 C(CH₃)₂ CH₃ H O Cl OH Ia1.653 C(CH₃)₂ CH₃ H O Br OH Ia1.654 C(CH₃)₂ CH₃ H O NO₂ OH Ia1.655 C(CH₃)₂ CH₃ H O CHF₂ OH Ia1.656 C(CH₃)₂ CH₃ H O CF₃ OH Ia1.657 C(CH₃)₂ CH₃ H O OCH₃ OH Ia1.658 C(CH₃)₂ CH₃ H O OCH₂CH₃ OH Ia1.659 C(CH₃)₂ CH₃ H O OCHF₂ OH Ia1.660 C(CH₃)₂ CH₃ H O OCF₃ OH Ia1.661 C(CH₃)₂ CH₃ CH₃ O SCH₃ OH Ia1.662 C(CH₃)₂ CH₃ CH₃ O SCH₂CH₃ OH Ia1.663 C(CH₃)₂ CH₃ CH₃ O SO₂CH₃ OH Ia1.664 C(CH₃)₂ CH₃ CH₃ O SO₂CH₂CH₃ OH Ia1.665 C(CH₃)₂ CH₃ CH₃ O SO₂CH(CH₃)₂ OH Ia1.666 C(CH₃)₂ CH₃ CH₃ O SO₂(CH₂)₂CH₃ OH Ia1.667 C(CH₃)₂ CH₃ CH₃ O Cl OH Ia1.668 C(CH₃)₂ CH₃ CH₃ O Br OH Ia1.669 C(CH₃)₂ CH₃ CH₃ O NO₂ OH Ia1.670 C(CH₃)₂ CH₃ CH₃ O CHF₂ OH Ia1.671 C(CH₃)₂ CH₃ CH₃ O CF₃ OH Ia1.672 C(CH₃)₂ CH₃ CH₃ O OCH₃ OH Ia1.673 C(CH₃)₂ CH₃ CH₃ O OCH₂CH₃ OH Ia1.674 C(CH₃)₂ CH₃ CH₃ O OCHF₂ OH Ia1.675 C(CH₃)₂ CH₃ CH₃ O OCF₃ OH Ia1.676 C(CH₃)₂ H H S SCH₃ OH Ia1.677 C(CH₃)₂ H H S SCH₂CH₃ OH Ia1.678 C(CH₃)₂ H H S SO₂CH₃ OH Ia1.679 C(CH₃)₂ H H S SO₂CH₂CH₃ OH Ia1.680 C(CH₃)₂ H H S SO₂CH(CH₃)₂ OH Ia1.681 C(CH₃)₂ H H S SO₂(CH₂)₂CH₃ OH Ia1.682 C(CH₃)₂ H H S Cl OH Ia1.683 C(CH₃)₂ H H S Br OH Ia1.684 C(CH₃)₂ H H S NO₂ OH Ia1.685 C(CH₃)₂ H H S CHF₂ OH Ia1.686 C(CH₃)₂ H H S CF₃ OH Ia1.687 C(CH₃)₂ H H S OCH₃ OH Ia1.688 C(CH₃)₂ H H S OCH₂CH₃ OH Ia1.689 C(CH₃)₂ H H S OCHF₂ OH Ia1.690 C(CH₃)₂ H H S OCF₃ OH Ia1.691 C(CH₃)₂ CH₃ H S SCH₃ OH Ia1.692 C(CH₃)₂ CH₃ H S SCH₂CH₃ OH Ia1.693 C(CH₃)₂ CH₃ H S SO₂CH₃ OH Ia1.694 C(CH₃)₂ CH₃ H S SO₂CH₂CH₃ OH Ia1.695 C(CH₃)₂ CH₃ H S SO₂CH(CH₃)₂ OH Ia1.696 C(CH₃)₂ CH₃ H S SO₂(CH₂)₂CH₃ OH Ia1.697 C(CH₃)₂ CH₃ H S Cl OH Ia1.698 C(CH₃)₂ CH₃ H S Br OH Ia1.699 C(CH₃)₂ CH₃ H S NO₂ OH Ia1.700 C(CH₃)₂ CH₃ H S CHF₂ OH Ia1.701 C(CH₃)₂ CH₃ H S CF₃ OH Ia1.702 C(CH₃)₂ CH₃ H S OCH₃ OH Ia1.703 C(CH₃)₂ CH₃ H S OCH₂CH₃ OH Ia1.704 C(CH₃)₂ CH₃ H S OCHF₂ OH Ia1.705 C(CH₃)₂ CH₃ H S OCF₃ OH Ia1.706 C(CH₃)₂ CH₃ CH₃ S SCH₃ OH Ia1.707 C(CH₃)₂ CH₃ CH₃ S SCH₂CH₃ OH Ia1.708 C(CH₃)₂ CH₃ CH₃ S SO₂CH₃ OH Ia1.709 C(CH₃)₂ CH₃ CH₃ S SO₂CH₂CH₃ OH Ia1.710 C(CH₃)₂ CH₃ CH₃ S SO₂CH(CH₃)₂ OH Ia1.711 C(CH₃)₂ CH₃ CH₃ S SO₂(CH₂)₂CH₃ OH Ia1.712 C(CH₃)₂ CH₃ CH₃ S Cl OH Ia1.713 C(CH₃)₂ CH₃ CH₃ S Br OH Ia1.714 C(CH₃)₂ CH₃ CH₃ S NO₂ OH Ia1.715 C(CH₃)₂ CH₃ CH₃ S CHF₂ OH Ia1.716 C(CH₃)₂ CH₃ CH₃ S CF₃ OH Ia1.717 C(CH₃)₂ CH₃ CH₃ S OCH₃ OH Ia1.718 C(CH₃)₂ CH₃ CH₃ S OCH₂CH₃ OH Ia1.719 C(CH₃)₂ CH₃ CH₃ S OCHF₂ OH Ia1.720 C(CH₃)₂ CH₃ CH₃ S OCF₃ OH Ia1.721 C(CH₃)₂ H H NCH₃ SCH₃ OH Ia1.722 C(CH₃)₂ H H NCH₃ SCH₂CH₃ OH Ia1.723 C(CH₃)₂ H H NCH₃ SO₂CH₃ OH Ia1.724 C(CH₃)₂ H H NCH₃ SO₂CH₂CH₃ OH Ia1.725 C(CH₃)₂ H H NCH₃ SO₂CH(CH₃)₂ OH Ia1.726 C(CH₃)₂ H H NCH₃ SO₂(CH₂)₂CH₃ OH Ia1.727 C(CH₃)₂ H H NCH₃ Cl OH Ia1.728 C(CH₃)₂ H H NCH₃ Br OH Ia1.729 C(CH₃)₂ H H NCH₃ NO₂ OH Ia1.730 C(CH₃)₂ H H NCH₃ CHF₂ OH Ia1.731 C(CH₃)₂ H H NCH₃ CF₃ OH Ia1.732 C(CH₃)₂ H H NCH₃ OCH₃ OH Ia1.733 C(CH₃)₂ H H NCH₃ OCH₂CH₃ OH Ia1.734 C(CH₃)₂ H H NCH₃ OCHF₂ OH Ia1.735 C(CH₃)₂ H H NCH₃ OCF₃ OH Ia1.736 C(CH₃)₂ CH₃ H NCH₃ SCH₃ OH Ia1.737 C(CH₃)₂ CH₃ H NCH₃ SCH₂CH₃ OH Ia1.738 C(CH₃)₂ CH₃ H NCH₃ SO₂CH₃ OH Ia1.739 C(CH₃)₂ CH₃ H NCH₃ SO₂CH₂CH₃ OH Ia1.740 C(CH₃)₂ CH₃ H NCH₃ SO₂CH(CH₃)₂ OH Ia1.741 C(CH₃)₂ CH₃ H NCH₃ SO₂(CH₂)₂CH₃ OH Ia1.742 C(CH₃)₂ CH₃ H NCH₃ Cl OH Ia1.743 C(CH₃)₂ CH₃ H NCH₃ Br OH Ia1.744 C(CH₃)₂ CH₃ H NCH₃ NO₂ OH Ia1.745 C(CH₃)₂ CH₃ H NCH₃ CHF₂ OH Ia1.746 C(CH₃)₂ CH₃ H NCH₃ CF₃ OH Ia1.747 C(CH₃)₂ CH₃ H NCH₃ OCH₃ OH Ia1.748 C(CH₃)₂ CH₃ H NCH₃ OCH₂CH₃ OH Ia1.749 C(CH₃)₂ CH₃ H NCH₃ OCHF₂ OH Ia1.750 C(CH₃)₂ CH₃ H NCH₃ OCF₃ OH Ia1.751 C(CH₃)₂ CH₃ CH₃ NCH₃ SCH₃ OH Ia1.752 C(CH₃)₂ CH₃ CH₃ NCH₃ SCH₂CH₃ OH Ia1.753 C(CH₃)₂ CH₃ CH₃ NCH₃ SO₂CH₃ OH Ia1.754 C(CH₃)₂ CH₃ CH₃ NCH₃ SO₂CH₂CH₃ OH Ia1.755 C(CH₃)₂ CH₃ CH₃ NCH₃ SO₂CH(CH₃)₂ OH Ia1.756 C(CH₃)₂ CH₃ CH₃ NCH₃ SO₂(CH₂)₂CH₃ OH Ia1.757 C(CH₃)₂ CH₃ CH₃ NCH₃ Cl OH Ia1.758 C(CH₃)₂ CH₃ CH₃ NCH₃ Br OH Ia1.759 C(CH₃)₂ CH₃ CH₃ NCH₃ NO₂ OH Ia1.760 C(CH₃)₂ CH₃ CH₃ NCH₃ CHF₂ OH Ia1.761 C(CH₃)₂ CH₃ CH₃ NCH₃ CF₃ OH Ia1.762 C(CH₃)₂ CH₃ CH₃ NCH₃ OCH₃ OH Ia1.763 C(CH₃)₂ CH₃ CH₃ NCH₃ OCH₂CH₃ OH Ia1.764 C(CH₃)₂ CH₃ CH₃ NCH₃ OCHF₂ OH Ia1.765 C(CH₃)₂ CH₃ CH₃ NCH₃ OCF₃ OH

Most particular preference is also given to the compounds of the formula Ia2, in particular to the compounds Ia2.1, to Ia2.765 which differ from the corresponding compounds Ia1.1 to Ia1.765 in that R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ia3, in particular to the compounds Ia3.1 to Ia3.765 which differ from the compounds Ia1.1 to Ia1.765 in that R¹³ is cyclopentyl.

Most particular preference is also given to the compounds of the formula Ia4, in particular to the compounds Ia4.1 to Ia4.765 which differ from the compounds Ia1.1 to Ia1.765 in that R¹³ is cyclopentyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ia5, in particular to the compounds Ia5.1 to Ia5.765 which differ from the compounds Ia1.1 to Ia1.765 in that R¹³ is cyclohexyl.

Most particular preference is also given to the compounds of the formula Ia6, in particular to the compounds Ia6.1 to Ia6.765 which differ from the compounds Ia1.1 to Ia1.765 in that R¹³ is cyclohexyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ia7, in particular to the compounds Ia7.1 to Ia7.765 which differ from the compounds Ia1.1 to Ia1.765 in that R¹³ is 2-norbornyl.

Most particular preference is also given to the compounds of the formula Ia8, in particular to the compounds Ia8.1 to Ia8.765 which differ from the compounds Ia1.1 to Ia1.765 in that R¹³ is 2-norbornyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ia9, in particular to the compounds Ia9.1 to Ia9.765 which differ from the compounds Ia1.1 to Ia1.765 in that R¹³ is 2-adamantyl.

Most particular preference is also given to the compounds of the formula Ia10, in particular to the compounds Ia10.1 to Ia10.765 which differ from the compounds Ia1.1 to Ia1.765 in that R¹³ is 2-adamantyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ia11, in particular to the compounds Ia11.1 to Ia11.765 which differ from the corresponding compounds Ia1.1 to Ia1.765 in that R¹ is methyl.

Most particular preference is also given to the compounds of the formula Ia12, in particular to the compounds Ia12.1 to Ia12.765 which differ from the corresponding compounds Ia1.1 to Ia1.765 in that R¹ is methyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ia13, in particular to the compounds Ia13.1 to Ia13.765 which differ from the compounds Ia1.1 to Ia1.765 in that R¹ is methyl and R¹³ is cyclopentyl.

Most particular preference is also given to the compounds of the formula Ia14, in particular to the compounds Ia14.1 to Ia14.765 which differ from the compounds Ia1.1 to Ia1.765 in that R¹ is methyl, R¹³ is cyclopentyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ia15, in particular to the compounds Ia15.1 to Ia15.765 which differ from the compounds Ia1.1 to Ia1.765 in that R¹ is methyl and R¹³ is cyclohexyl.

Most particular preference is also given to the compounds of the formula Ia16, in particular to the compounds Ia16.1 to Ia16.765 which differ from the compounds Ia1.1 to Ia1.765 in that R¹ is methyl, R¹³ is cyclohexyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ia17, in particular to the compounds Ia17.1 to Ia17.765 which differ from the compounds Ia1.1 to Ia1.765 in that R¹ is methyl and R¹³ is 2-norbornyl.

Most particular preference is also given to the compounds of the formula Ia18, in particular to the compounds Ia18.1 to Ia18.765 which differ from the compounds Ia1.1 to Ia1.765 in that R¹ is methyl, R¹² is 2-norbornyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ia19, in particular to the compounds Ia19.1 to Ia19.765 which differ from the compounds Ia1.1 to Ia1.765 in that R¹ is methyl and R¹³ is 2-adamantyl.

Most particular preference is also given to the compounds of the formula Ia20, in particular to the compounds Ia20.1 to Ia20.765 which differ from the compounds Ia1.1 to Ia1.765 in that R¹ is methyl, R¹³ is 2-adamantyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ia21, in particular to the compounds Ia21.1 to Ia21.765 which differ from the corresponding compounds Ia1.1 to Ia1.765 in that R¹ is methoxy.

Most particular preference is also given to the compounds of the formula Ia22, in particular to the compounds Ia22.1 to Ia22.765 which differ from the corresponding compounds Ia1.1 to Ia1.765 in that R¹ is methoxy and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ia23, in particular to the compounds Ia23.1 to Ia23.765 which differ from the compounds Ia1.1 to Ia1.765 in that R¹ is methoxy and R¹³ is cyclopentyl.

Most particuiar preference is also given to the compounds of the formula Ia24, in particular to the compounds Ia24.1 to Ia24.765 which differ from the compounds Ia1.1 to Ia1.765 in that R¹ is methoxy, R¹³ is cyclopentyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ia25, in particular to the compounds Ia25.1 to Ia25.765 which differ from the compounds Ia1.1 to Ia1.765 in that R¹ is methoxy and R¹³ is cyclohexyl.

Most particular preference is also given to the compounds of the formula Ia26, in particular to the compounds Ia26.1 to Ia26.765 which differ from the compounds Ia1.1 to Ia1.765 in that R¹ is methoxy, R¹³ is cyclohexyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ia27, in particular to the compounds Ia27.1 to Ia27.765 which differ from the compounds Ia1.1 to Ia1.765 in that R¹ is methoxy and R¹³ is 2-norbornyl.

Most particular preference is also given to the compounds of the formula Ia28, in particular to the compounds Ia28.1 to Ia28.765 which differ from the compounds Ia1.1 to Ia1.765 in that R¹ is methoxy, R¹³ is norbornyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ia29, in particular to the compounds Ia29.1 to Ia29.765 which differ from the compounds Ia1.1 to Ia1.765 in that R¹ is methoxy and R¹³ is 2-adamantyl.

Most particular preference is also given to the compounds of the formula Ia30, in particular to the compounds Ia30.1 to Ia30.765 which differ from the compounds Ia1.1 to Ia1.765 in that R¹ is methoxy, R¹³ is 2-adamantyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ib1 (=I where R¹=Cl, R³ and R⁹ or R³ and R¹¹ together form a bond, R¹³=cyclo-C₃H₅ and R⁵ and R¹⁴=H), in particular to the compounds Ib1.1 to Ib1.420 of Table 2 where the radical definitions X, Y and R¹ to R¹⁴ are of particular importance for the compounds according to the invention not only in combination with one another but also in each case on their own.

TABLE 2 X R² Y R⁴ R¹² Ib1.1 O H CH SCH₃ OH Ib1.2 O H CH SCH₂CH₃ OH Ib1.3 O H CH SO₂CH₃ OH Ib1.4 O H CH SO₂CH₂CH₃ OH Ib1.5 O H CH SO₂CH(CH₃)₂ OH Ib1.6 O H CH SO₂(CH₂)₂CH₃ OH Ib1.7 O H CH Cl OH Ib1.8 O H CH Br OH Ib1.9 O H CH NO₂ OH Ib1.10 O H CH CHF₂ OH Ib1.11 O H CH CF₃ OH Ib1.12 O H CH OCH₃ OH Ib1.13 O H CH OCH₂CH₃ OH Ib1.14 O H CH OCHF₂ OH Ib1.15 O H CH OCF₃ OH Ib1.16 O CH₃ CH SCH₃ OH Ib1.17 O CH₃ CH SCH₂CH₃ OH Ib1.18 O CH₃ CH SO₂CH₃ OH Ib1.19 O CH₃ CH SO₂CH₂CH₃ OH Ib1.20 O CH₃ CH SO₂CH(CH₃)₂ OH Ib1.21 O CH₃ CH SO₂(CH₂)₂CH₃ OH Ib1.22 O CH₃ CH Cl OH Ib1.23 O CH₃ CH Br OH Ib1.24 O CH₃ CH NO₂ OH Ib1.25 O CH₃ CH CHF₂ OH Ib1.26 O CH₃ CH CF₃ OH Ib1.27 O CH₃ CH OCH₃ OH Ib1.28 O CH₃ CH OCH₂CH₃ OH Ib1.29 O CH₃ CH OCHF₂ OH Ib1.30 O CH₃ CH OCF₃ OH Ib1.31 O CH₂CH₃ CH SCH₃ OH Ib1.32 O CH₂CH₃ CH SCH₂CH₃ OH Ib1.33 O CH₂CH₃ CH SO₂CH₃ OH Ib1.34 O CH₂CH₃ CH SO₂CH₂CH₃ OH Ib1.35 O CH₂CH₃ CH SO₂CH(CH₃)₂ OH Ib1.36 O CH₂CH₃ CH SO₂(CH₂)₂CH₃ OH Ib1.37 O CH₂CH₃ CH Cl OH Ib1.38 O CH₂CH₃ CH Br OH Ib1.39 O CH₂CH₃ CH NO₂ OH Ib1.40 O CH₂CH₃ CH CHF₂ OH Ib1.41 O CH₂CH₃ CH CF₃ OH Ib1.42 O CH₂CH₃ CH OCH₃ OH Ib1.43 O CH₂CH₃ CH OCH₂CH₃ OH Ib1.44 O CH₂CH₃ CH OCHF₂ OH Ib1.45 O CH₂CH₃ CH OCF₃ OH Ib1.46 O CH₂Cl CH SCH₃ OH Ib1.47 O CH₂Cl CH SCH₂CH₃ OH Ib1.48 O CH₂Cl CH SO₂CH₃ OH Ib1.49 O CH₂Cl CH SO₂CH₂CH₃ OH Ib1.50 O CH₂Cl CH SO₂CH(CH₃)₂ OH Ib1.51 O CH₂Cl CH SO₂(CH₂)₂CH₃ OH Ib1.52 O CH₂Cl CH Cl OH Ib1.53 O CH₂Cl CH Br OH Ib1.54 O CH₂Cl CH NO₂ OH Ib1.55 O CH₂Cl CH CHF₂ OH Ib1.56 O CH₂Cl CH CF₃ OH Ib1.57 O CH₂Cl CH OCH₃ OH Ib1.58 O CH₂Cl CH OCH₂CH₃ OH Ib1.59 O CH₂Cl CH OCHF₂ OH Ib1.60 O CH₂Cl CH OCF₃ OH Ib1.61 O H C(CH₃) SCH₃ OH Ib1.62 O H C(CH₃) SCH₂CH₃ OH Ib1.63 O H C(CH₃) SO₂CH₃ OH Ib1.64 O H C(CH₃) SO₂CH₂CH₃ OH Ib1.65 O H C(CH₃) SO₂CH(CH₃)₂ OH Ib1.66 O H C(CH₃) SO₂(CH₂)₂CH₃ OH Ib1.67 O H C(CH₃) Cl OH Ib1.68 O H C(CH₃) Br OH Ib1.69 O H C(CH₃) NO₂ OH Ib1.70 O H C(CH₃) CHF₂ OH Ib1.71 O H C(CH₃) CF₃ OH Ib1.72 O H C(CH₃) OCH₃ OH Ib1.73 O H C(CH₃) OCH₂CH₃ OH Ib1.74 O H C(CH₃) OCHF₂ OH Ib1.75 O H C(CH₃) OCF₃ OH Ib1.76 O CH₃ C(CH₃) SCH₃ OH Ib1.77 O CH₃ C(CH₃) SCH₂CH₃ OH Ib1.78 O CH₃ C(CH₃) SO₂CH₃ OH Ib1.79 O CH₃ C(CH₃) SO₂CH₂CH₃ OH Ib1.80 O CH₃ C(CH₃) SO₂CH(CH₃)₂ OH Ib1.81 O CH₃ C(CH₃) SO₂(CH₂)₂CH₃ OH Ib1.82 O CH₃ C(CH₃) Cl OH Ib1.83 O CH₃ C(CH₃) Br OH Ib1.84 O CH₃ C(CH₃) NO₂ OH Ib1.85 O CH₃ C(CH₃) CHF₂ OH Ib1.86 O CH₃ C(CH₃) CF₃ OH Ib1.87 O CH₃ C(CH₃) OCH₃ OH Ib1.88 O CH₃ C(CH₃) OCH₂CH₃ OH Ib1.89 O CH₃ C(CH₃) OCHF₂ OH Ib1.90 O CH₃ C(CH₃) OCF₃ OH Ib1.91 O CH₂CH₃ C(CH₃) SCH₃ OH Ib1.92 O CH₂CH₃ C(CH₃) SCH₂CH₃ OH Ib1.93 O CH₂CH₃ C(CH₃) SO₂CH₃ OH Ib1.94 O CH₂CH₃ C(CH₃) SO₂CH₂CH₃ OH Ib1.95 O CH₂CH₃ C(CH₃) SO₂CH(CH₃)₂ OH Ib1.96 O CH₂CH₃ C(CH₃) SO₂(CH₂)₂CH₃ OH Ib1.97 O CH₂CH₃ C(CH₃) Cl OH Ib1.98 O CH₂CH₃ C(CH₃) Br OH Ib1.99 O CH₂CH₃ C(CH₃) NO₂ OH Ib1.100 O CH₂CH₃ C(CH₃) CHF₂ OH Ib1.101 O CH₂CH₃ C(CH₃) CF₃ OH Ib1.102 O CH₂CH₃ C(CH₃) OCH₃ OH Ib1.103 O CH₂CH₃ C(CH₃) OCH₂CH₃ OH Ib1.104 O CH₂CH₃ C(CH₃) OCHF₂ OH Ib1.105 O CH₂CH₃ C(CH₃) OCF₃ OH Ib1.106 O CH₂Cl C(CH₃) SCH₃ OH Ib1.107 O CH₂Cl C(CH₃) SCH₂CH₃ OH Ib1.108 O CH₂Cl C(CH₃) SO₂CH₃ OH Ib1.109 O CH₂Cl C(CH₃) SO₂CH₂CH₃ OH Ib1.110 O CH₂Cl C(CH₃) SO₂CH(CH₃)₂ OH Ib1.111 O CH₂Cl C(CH₃) SO₂(CH₂)₂CH₃ OH Ib1.112 O CH₂Cl C(CH₃) Cl OH Ib1.113 O CH₂Cl C(CH₃) Br OH Ib1.114 O CH₂Cl C(CH₃) NO₂ OH Ib1.115 O CH₂Cl C(CH₃) CHF₂ OH Ib1.116 O CH₂Cl C(CH₃) CF₃ OH Ib1.117 O CH₂Cl C(CH₃) OCH₃ OH Ib1.118 O CH₂Cl C(CH₃) OCH₂CH₃ OH Ib1.119 O CH₂Cl C(CH₃) OCHF₂ OH Ib1.120 O CH₂Cl C(CH₃) OCF₃ OH Ib1.121 O H C(CH₂CH₃) SCH₃ OH Ib1.122 O H C(CH₂CH₃) SCH₂CH₃ OH Ib1.123 O H C(CH₂CH₃) SO₂CH₃ OH Ib1.124 O H C(CH₂CH₃) SO₂CH₂CH₃ OH Ib1.125 O H C(CH₂CH₃) SO₂CH(CH₃)₂ OH Ib1.126 O H C(CH₂CH₃) SO₂(CH₂)₂CH₃ OH Ib1.127 O H C(CH₂CH₃) Cl OH Ib1.128 O H C(CH₂CH₃) Br OH Ib1.129 O H C(CH₂CH₃) NO₂ OH Ib1.130 O H C(CH₂CH₃) CHF₂ OH Ib1.131 O H C(CH₂CH₃) CF₃ OH Ib1.132 O H C(CH₂CH₃) OCH₃ OH Ib1.133 O H C(CH₂CH₃) OCH₂CH₃ OH Ib1.134 O H C(CH₂CH₃) OCHF₂ OH Ib1.135 O H C(CH₂CH₃) OCF₃ OH Ib1.136 O CH₃ C(CH₂CH₃) SCH₃ OH Ib1.137 O CH₃ C(CH₂CH₃) SCH₂CH₃ OH Ib1.138 O CH₃ C(CH₂CH₃) SO₂CH₃ OH Ib1.139 O CH₃ C(CH₂CH₃) SO₂CH₂CH₃ OH Ib1.140 O CH₃ C(CH₂CH₃) SO₂CH(CH₃)₂ OH Ib1.141 O CH₃ C(CH₂CH₃) SO₂(CH₂)₂CH₃ OH Ib1.142 O CH₃ C(CH₂CH₃) Cl OH Ib1.143 O CH₃ C(CH₂CH₃) Br OH Ib1.144 O CH₃ C(CH₂CH₃) NO₂ OH Ib1.145 O CH₃ C(CH₂CH₃) CHF₂ OH Ib1.146 O CH₃ C(CH₂CH₃) CF₃ OH Ib1.147 O CH₃ C(CH₂CH₃) OCH₃ OH Ib1.148 O CH₃ C(CH₂CH₃) OCH₂CH₃ OH Ib1.149 O CH₃ C(CH₂CH₃) OCHF₂ OH Ib1.150 O CH₃ C(CH₂CH₃) OCF₃ OH Ib1.151 O CH₂CH₃ C(CH₂CH₃) SCH₃ OH Ib1.152 O CH₂CH₃ C(CH₂CH₃) SCH₂CH₃ OH Ib1.153 O CH₂CH₃ C(CH₂CH₃) SO₂CH₃ OH Ib1.154 O CH₂CH₃ C(CH₂CH₃) SO₂CH₂CH₃ OH Ib1.155 O CH₂CH₃ C(CH₂CH₃) SO₂CH(CH₃)₂ OH Ib1.156 O CH₂CH₃ C(CH₂CH₃) SO₂(CH₂)₂CH₃ OH Ib1.157 O CH₂CH₃ C(CH₂CH₃) Cl OH Ib1.158 O CH₂CH₃ C(CH₂CH₃) Br OH Ib1.159 O CH₂CH₃ C(CH₂CH₃) NO₂ OH Ib1.160 O CH₂CH₃ C(CH₂CH₃) CHF₂ OH Ib1.161 O CH₂CH₃ C(CH₂CH₃) CF₃ OH Ib1.162 O CH₂CH₃ C(CH₂CH₃) OCH₃ OH Ib1.163 O CH₂CH₃ C(CH₂CH₃) OCH₂CH₃ OH Ib1.164 O CH₂CH₃ C(CH₂CH₃) OCHF₂ OH Ib1.165 O CH₂CH₃ C(CH₂CH₃) OCF₃ OH Ib1.166 O CH₂Cl C(CH₂CH₃) SCH₃ OH Ib1.167 O CH₂Cl C(CH₂CH₃) SCH₂CH₃ OH Ib1.168 O CH₂Cl C(CH₂CH₃) SO₂CH₃ OH Ib1.169 O CH₂Cl C(CH₂CH₃) SO₂CH₂CH₃ OH Ib1.170 O CH₂Cl C(CH₂CH₃) SO₂CH(CH₃)₂ OH Ib1.171 O CH₂Cl C(CH₂CH₃) SO₂(CH₂)₂CH₃ OH Ib1.172 O CH₂Cl C(CH₂CH₃) Cl OH Ib1.173 O CH₂Cl C(CH₂CH₃) Br OH Ib1.174 O CH₂Cl C(CH₂CH₃) NO₃ OH Ib1.175 O CH₂Cl C(CH₂CH₃) CHF₂ OH Ib1.176 O CH₂Cl C(CH₂CH₃) CF₃ OH Ib1.177 O CH₂Cl C(CH₂CH₃) OCH₃ OH Ib1.178 O CH₂Cl C(CH₂CH₃) OCH₂CH₃ OH Ib1.179 O CH₂Cl C(CH₂CH₃) OCHF₂ OH Ib1.180 O CH₂Cl C(CH₂CH₃) OCF₃ OH Ib1.181 NCH₃ H CH SCH₃ OH Ib1.182 NCH₃ H CH SCH₂CH₃ OH Ib1.183 NCH₃ H CH SO₂CH₃ OH Ib1.184 NCH₃ H CH SO₂CH₂CH₃ OH Ib1.185 NCH₃ H CH SO₂CH(CH₃)₂ OH Ib1.186 NCH₃ H CH SO₂(CH₂)₂CH₃ OH Ib1.187 NCH₃ H CH Cl OH Ib1.188 NCH₃ H CH Br OH Ib1.189 NCH₃ H CH NO₂ OH Ib1.190 NCH₃ H CH CHF₂ OH Ib1.191 NCH₃ H CH CF₃ OH Ib1.192 NCH₃ H CH OCH₃ OH Ib1.193 NCH₃ H CH OCH₂CH₃ OH Ib1.194 NCH₃ H CH OCHF₂ OH Ib1.195 NCH₃ H CH OCF₃ OH Ib1.196 NCH₃ CH₃ CH SCH₃ OH Ib1.197 NCH₃ CH₃ CH SCH₂CH₃ OH Ib1.198 NCH₃ CH₃ CH SO₂CH₃ OH Ib1.199 NCH₃ CH₃ CH SO₂CH₂CH₃ OH Ib1.200 NCH₃ CH₃ CH SO₂CH(CH₃)₂ OH Ib1.201 NCH₃ CH₃ CH SO₂(CH₂)₂CH₃ OH Ib1.202 NCH₃ CH₃ CH Cl OH Ib1.203 NCH₃ CH₃ CH Br OH Ib1.204 NCH₃ CH₃ CH NO₂ OH Ib1.205 NCH₃ CH₃ CH CHF₂ OH Ib1.206 NCH₃ CH₃ CH CF₃ OH Ib1.207 NCH₃ CH₃ CH OCH₃ OH Ib1.208 NCH₃ CH₃ CH OCH₂CH₃ OH Ib1.209 NCH₃ CH₃ CH OCHF₂ OH Ib1.210 NCH₃ CH₃ CH OCF₃ OH Ib1.211 NCH₃ CH₂CH₃ CH SCH₃ OH Ib1.212 NCH₃ CH₂CH₃ CH SCH₂CH₃ OH Ib1.213 NCH₃ CH₂CH₃ CH SO₂CH₃ OH Ib1.214 NCH₃ CH₂CH₃ CH SO₂CH₂CH₃ OH Ib1.215 NCH₃ CH₂CH₃ CH SO₂CH(CH₃)₂ OH Ib1.216 NCH₃ CH₂CH₃ CH SO₂(CH₂)₂CH₃ OH Ib1.217 NCH₃ CH₂CH₃ CH Cl OH Ib1.218 NCH₃ CH₂CH₃ CH Br OH Ib1.219 NCH₃ CH₂CH₃ CH NO₂ OH Ib1.220 NCH₃ CH₂CH₃ CH CHF₂ OH Ib1.221 NCH₃ CH₂CH₃ CH CF₃ OH Ib1.222 NCH₃ CH₂CH₃ CH OCH₃ OH Ib1.223 NCH₃ CH₂CH₃ CH OCH₂CH₃ OH Ib1.224 NCH₃ CH₂CH₃ CH OCHF₂ OH Ib1.225 NCH₃ CH₂CH₃ CH OCF₃ OH Ib1.226 NCH₃ CH₂Cl CH SCH₃ OH Ib1.227 NCH₃ CH₂Cl CH SCH₂CH₃ OH Ib1.228 NCH₃ CH₂Cl CH SO₂CH₃ OH Ib1.229 NCH₃ CH₂Cl CH SO₂CH₂CH₃ OH Ib1.230 NCH₃ CH₂Cl CH SO₂CH(CH₃)₂ OH Ib1.231 NCH₃ CH₂Cl CH SO₂(CH₂)₂CH₃ OH Ib1.232 NCH₃ CH₂Cl CH Cl OH Ib1.233 NCH₃ CH₂Cl CH Br OH Ib1.234 NCH₃ CH₂Cl CH NO₂ OH Ib1.235 NCH₃ CH₂Cl CH CHF₂ OH Ib1.236 NCH₃ CH₂Cl CH CF₃ OH Ib1.237 NCH₃ CH₂Cl CH OCH₃ OH Ib1.238 NCH₃ CH₂Cl CH OCH₂CH₃ OH Ib1.239 NCH₃ CH₂Cl CH OCHF₂ OH Ib1.240 NCH₃ CH₂Cl CH OCF₃ OH Ib1.241 NCH₃ H C(CH₃) SCH₃ OH Ib1.242 NCH₃ H C(CH₃) SCH₂CH₃ OH Ib1.243 NCH₃ H C(CH₃) SO₂CH₃ OH Ib1.244 NCH₃ H C(CH₃) SO₂CH₂CH₃ OH Ib1.245 NCH₃ H C(CH₃) SO₂CH(CH₃)₂ OH Ib1.246 NCH₃ H C(CH₃) SO₂(CH₂)₂CH₃ OH Ib1.247 NCH₃ H C(CH₃) Cl OH Ib1.248 NCH₃ H C(CH₃) Br OH Ib1.249 NCH₃ H C(CH₃) NO₂ OH Ib1.250 NCH₃ H C(CH₃) CHF₂ OH Ib1.251 NCH₃ H C(CH₃) CF₃ OH Ib1.252 NCH₃ H C(CH₃) OCH₃ OH Ib1.253 NCH₃ H C(CH₃) OCH₂CH₃ OH Ib1.254 NCH₃ H C(CH₃) OCHF₂ OH Ib1.255 NCH₃ H C(CH₃) OCF₃ OH Ib1.256 NCH₃ CH₃ C(CH₃) SCH₃ OH Ib1.257 NCH₃ CH₃ C(CH₃) SCH₂CH₃ OH Ib1.258 NCH₃ CH₃ C(CH₃) SO₂CH₃ OH Ib1.259 NCH₃ CH₃ C(CH₃) SO₂CH₂CH₃ OH Ib1.260 NCH₃ CH₃ C(CH₃) SO₂CH(CH₃)₂ OH Ib1.261 NCH₃ CH₃ C(CH₃) SO₂(CH₂)₂CH₃ OH Ib1.262 NCH₃ CH₃ C(CH₃) Cl OH Ib1.263 NCH₃ CH₃ C(CH₃) Br OH Ib1.264 NCH₃ CH₃ C(CH₃) NO₂ OH Ib1.265 NCH₃ CH₃ C(CH₃) CHF₂ OH Ib1.266 NCH₃ CH₃ C(CH₃) CF₃ OH Ib1.267 NCH₃ CH₃ C(CH₃) OCH₃ OH Ib1.268 NCH₃ CH₃ C(CH₃) OCH₂CH₃ OH Ib1.269 NCH₃ CH₃ C(CH₃) OCHF₂ OH Ib1.270 NCH₃ CH₃ C(CH₃) OCF₃ OH Ib1.271 NCH₃ CH₂CH₃ C(CH₃) SCH₃ OH Ib1.272 NCH₃ CH₂CH₃ C(CH₃) SCH₂CH₃ OH Ib1.273 NCH₃ CH₂CH₃ C(CH₃) SO₂CH₃ OH Ib1.274 NCH₃ CH₂CH₃ C(CH₃) SO₂CH₂CH₃ OH Ib1.275 NCH₃ CH₂CH₃ C(CH₃) SO₂CH(CH₃)₂ OH Ib1.276 NCH₃ CH₂CH₃ C(CH₃) SO₂(CH₂)₂CH₃ OH Ib1.277 NCH₃ CH₂CH₃ C(CH₃) Cl OH Ib1.278 NCH₃ CH₂CH₃ C(CH₃) Br OH Ib1.279 NCH₃ CH₂CH₃ C(CH₃) NO₂ OH Ib1.280 NCH₃ CH₂CH₃ C(CH₃) CHF₂ OH Ib1.281 NCH₃ CH₂CH₃ C(CH₃) CF₃ OH Ib1.282 NCH₃ CH₂CH₃ C(CH₃) OCH₃ OH Ib1.283 NCH₃ CH₂CH₃ C(CH₃) OCH₂CH₃ OH Ib1.284 NCH₃ CH₂CH₃ C(CH₃) OCHF₂ OH Ib1.285 NCH₃ CH₂CH₃ C(CH₃) OCF₃ OH Ib1.286 NCH₃ CH₂CH₃ C(CH₃) SCH₃ OH Ib1.287 NCH₃ CH₂Cl C(CH₃) SCH₂CH₃ OH Ib1.288 NCH₃ CH₂Cl C(CH₃) SO₂CH₃ OH Ib1.289 NCH₃ CH₂Cl C(CH₃) SO₂CH₂CH₃ OH Ib1.290 NCH₃ CH₂Cl C(CH₃) SO₂CH(CH₃)₂ OH Ib1.291 NCH₃ CH₂Cl C(CH₃) SO₂(CH₂)₂CH₃ OH Ib1.292 NCH₃ CH₂Cl C(CH₃) Cl OH Ib1.293 NCH₃ CH₂Cl C(CH₃) Br OH Ib1.294 NCH₃ CH₂Cl C(CH₃) NO₂ OH Ib1.295 NCH₃ CH₂Cl C(CH₃) CHF₂ OH Ib1.296 NCH₃ CH₂Cl C(CH₃) CF₃ OH Ib1.297 NCH₃ CH₂Cl C(CH₃) OCH₃ OH Ib1.298 NCH₃ CH₂Cl C(CH₃) OCH₂CH₃ OH Ib1.299 NCH₃ CH₂Cl C(CH₃) OCHF₂ OH Ib1.300 NCH₃ CH₂Cl C(CH₃) OCF₃ OH Ib1.301 NCH₃ H C(CH₂CH₃) SCH₃ OH Ib1.302 NCH₃ H C(CH₂CH₃) SCH₂CH₃ OH Ib1.303 NCH₃ H C(CH₂CH₃) SO₂CH₃ OH Ib1.304 NCH₃ H C(CH₂CH₃) SO₂CH₂CH₃ OH Ib1.305 NCH₃ H C(CH₂CH₃) SO₂CH(CH₃)₂ OH Ib1.306 NCH₃ H C(CH₂CH₃) SO₂(CH₂)₂CH₃ OH Ib1.307 NCH₃ H C(CH₂CH₃) Cl OH Ib1.308 NCH₃ H C(CH₂CH₃) Br OH Ib1.309 NCH₃ H C(CH₂CH₃) NO₂ OH Ib1.310 NCH₃ H C(CH₂CH₃) CHF₂ OH Ib1.311 NCH₃ H C(CH₂CH₃) CF₃ OH Ib1.312 NCH₃ H C(CH₂CH₃) OCH₃ OH Ib1.313 NCH₃ H C(CH₂CH₃) OCH₂CH₃ OH Ib1.314 NCH₃ H C(CH₂CH₃) OCHF₂ OH Ib1.315 NCH₃ H C(CH₂CH₃) OCF₃ OH Ib1.316 NCH₃ CH₃ C(CH₂CH₃) SCH₃ OH Ib1.317 NCH₃ CH₃ C(CH₂CH₃) SCH₂CH₃ OH Ib1.318 NCH₃ CH₃ C(CH₂CH₃) SO₂CH₃ OH Ib1.319 NCH₃ CH₃ C(CH₂CH₃) SO₂CH₂CH₃ OH Ib1.320 NCH₃ CH₃ C(CH₂CH₃) SO₂CH(CH₃)₂ OH Ib1.321 NCH₃ CH₃ C(CH₂CH₃) SO₂(CH₂)₂CH₃ OH Ib1.322 NCH₃ CH₃ C(CH₂CH₃) Cl OH Ib1.323 NCH₃ CH₃ C(CH₂CH₃) Br OH Ib1.324 NCH₃ CH₃ C(CH₂CH₃) NO₂ OH Ib1.325 NCH₃ CH₃ C(CH₂CH₃) CHF₂ OH Ib1.326 NCH₃ CH₃ C(CH₂CH₃) CF₃ OH Ib1.327 NCH₃ CH₃ C(CH₂CH₃) OCH₃ OH Ib1.329 NCH₃ CH₃ C(CH₂CH₃) OCH₂CH₃ OH Ib1.329 NCH₃ CH₃ C(CH₂CH₃) OCHF₂ OH Ib1.330 NCH₃ CH₃ C(CH₂CH₃) OCF₃ OH Ib1.331 NCH₃ CH₂CH₃ C(CH₂CH₃) SCH₃ OH Ib1.332 NCH₃ CH₂CH₃ C(CH₂CH₃) SCH₂CH₃ OH Ib1.333 NCH₃ CH₂CH₃ C(CH₂CH₃) SO₂CH₃ OH Ib1.334 NCH₃ CH₂CH₃ C(CH₂CH₃) SO₂CH₂CH₃ OH Ib1.335 NCH₃ CH₂CH₃ C(CH₂CH₃) SO₂CH(CH₃)₂ OH Ib1.336 NCH₃ CH₂CH₃ C(CH₂CH₃) SO₂(CH₂)₂CH₃ OH Ib1.337 NCH₃ CH₂CH₃ C(CH₂CH₃) Cl OH Ib1.338 NCH₃ CH₂CH₃ C(CH₂CH₃) Br OH Ib1.339 NCH₃ CH₂CH₃ C(CH₂CH₃) NO₂ OH Ib1.340 NCH₃ CH₂CH₃ C(CH₂CH₃) CHF₂ OH Ib1.341 NCH₃ CH₂CH₃ C(CH₂CH₃) CF₃ OH Ib1.342 NCH₃ CH₂CH₃ C(CH₂CH₃) OCH₃ OH Ib1.343 NCH₃ CH₂CH₃ C(CH₂CH₃) OCH₂CH₃ OH Ib1.344 NCH₃ CH₂CH₃ C(CH₂CH₃) OCHF₂ OH Ib1.345 NCH₃ CH₂CH₃ C(CH₂CH₃) OCF₃ OH Ib1.346 NCH₃ CH₂Cl C(CH₂CH₃) SCH₃ OH Ib1.347 NCH₃ CH₂Cl C(CH₂CH₃) SCH₂CH₃ OH Ib1.348 NCH₃ CH₂Cl C(CH₂CH₃) SO₂CH₃ OH Ib1.349 NCH₃ CH₂Cl C(CH₂CH₃) SO₂CH₂CH₃ OH Ib1.350 NCH₃ CH₂Cl C(CH₂CH₃) SO₂CH(CH₃)₂ OH Ib1.351 NCH₃ CH₂Cl C(CH₂CH₃) SO₂(CH₂)₂CH₃ OH Ib1.352 NCH₃ CH₂Cl C(CH₂CH₃) Cl OH Ib1.353 NCH₃ CH₂Cl C(CH₂CH₃) Br OH Ib1.354 NCH₃ CH₂Cl C(CH₂CH₃) NO₂ OH Ib1.355 NCH₃ CH₂Cl C(CH₂CH₃) CHF₂ OH Ib1.356 NCH₃ CH₂Cl C(CH₂CH₃) CF₃ OH Ib1.357 NCH₃ CH₂Cl C(CH₂CH₃) OCH₃ OH Ib1.358 NCH₃ CH₂Cl C(CH₂CH₃) OCH₂CH₃ OH Ib1.359 NCH₃ CH₂Cl C(CH₂CH₃) OCHF₂ OH Ib1.360 NCH₃ CH₂Cl C(CH₂CH₃) OCF₃ OH Ib1.361 NCH₃ H N SCH₃ OH Ib1.362 NCH₃ H N SCH₂CH₃ OH Ib1.363 NCH₃ H N SO₂CH₃ OH Ib1.364 NCH₃ H N SO₂CH₂CH₃ OH Ib1.365 NCH₃ H N SO₂CH(CH₃)₂ OH Ib1.366 NCH₃ H N SO₂(CH₂)₂CH₃ OH Ib1.367 NCH₃ H N Cl OH Ib1.368 NCH₃ H N Br OH Ib1.369 NCH₃ H N NO₂ OH Ib1.370 NCH₃ H N CHF₂ OH Ib1.371 NCH₃ H N CF₃ OH Ib1.372 NCH₃ H N OCH₃ OH Ib1.373 NCH₃ H N OCH₂CH₃ OH Ib1.374 NCH₃ H N OCHF₂ OH Ib1.375 NCH₃ H N OCF₃ OH Ib1.376 NCH₃ CH₃ N SCH₃ OH Ib1.377 NCH₃ CH₃ N SCH₂CH₃ OH Ib1.378 NCH₃ CH₃ N SO₂CH₃ OH Ib1.379 NCH₃ CH₃ N SO₂CH₂CH₃ OH Ib1.380 NCH₃ CH₃ N SO₂CH(CH₃)₂ OH Ib1.381 NCH₃ CH₃ N SO₂(CH₂)₂CH₃ OH Ib1.382 NCH₃ CH₃ N Cl OH Ib1.383 NCH₃ CH₃ N Br OH Ib1.384 NCH₃ CH₃ N NO₂ OH Ib1.385 NCH₃ CH₃ N CHF₂ OH Ib1.386 NCH₃ CH₃ N CF₃ OH Ib1.387 NCH₃ CH₃ N OCH₃ OH Ib1.388 NCH₃ CH₃ N OCH₂CH₃ OH Ib1.389 NCH₃ CH₃ N OCHF₂ OH Ib1.390 NCH₃ CH₃ N OCF₃ OH Ib1.391 NCH₃ CH₂CH₃ N SCH₃ OH Ib1.392 NCH₃ CH₂CH₃ N SCH₂CH₃ OH Ib1.393 NCH₃ CH₂CH₃ N SO₂CH₃ OH Ib1.394 NCH₃ CH₂CH₃ N SO₂CH₂CH₃ OH Ib1.395 NCH₃ CH₂CH₃ N SO₂CH(CH₃)₂ OH Ib1.396 NCH₃ CH₂CH₃ N SO₂(CH₂)₂CH₃ OH Ib1.397 NCH₃ CH₂CH₃ N Cl OH Ib1.398 NCH₃ CH₂CH₃ N Br OH Ib1.399 NCH₃ CH₂CH₃ N NO₃ OH Ib1.400 NCH₃ CH₂CH₃ N CHF₂ OH Ib1.401 NCH₃ CH₂CH₃ N CF₃ OH Ib1.402 NCH₃ CH₂CH₃ N OCH₃ OH Ib1.403 NCH₃ CH₂CH₃ N OCH₂CH₃ OH Ib1.404 NCH₃ CH₂CH₃ N OCHF₂ OH Ib1.405 NCH₃ CH₂CH₃ N OCF₃ OH Ib1.406 NCH₃ CH₂Cl N SCH₃ OH Ib1.407 NCH₃ CH₂Cl N SCH₂CH₃ OH Ib1.408 NCH₃ CH₂Cl N SO₂CH₃ OH Ib1.409 NCH₃ CH₂Cl N SO₂CH₂CH₃ OH Ib1.410 NCH₃ CH₂Cl N SO₂CH(CH₃)₂ OH Ib1.411 NCH₃ CH₂Cl N SO₂(CH₂)₂CH₃ OH Ib1.412 NCH₃ CH₂Cl N Cl OH Ib1.413 NCH₃ CH₂Cl N Br OH Ib1.414 NCH₃ CH₂Cl N NO₂ OH Ib1.415 NCH₃ CH₂Cl N CHF₂ OH Ib1.416 NCH₃ CH₂Cl N CF₃ OH Ib1.417 NCH₃ CH₂Cl N OCH₃ OH Ib1.418 NCH₃ CH₂Cl N OCH₂CH₃ OH Ib1.419 NCH₃ CH₂Cl N OCHF₂ OH Ib1.420 NCH₃ CH₂Cl N OCF₃ OH

Most particular preference is also given to the compounds of the formula Ib2, in particular to the compounds Ib2.1 to Ib2.420 which differ from the corresponding compounds Ib1.1 to Ib1.420 in that R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ib3, in particular to the compounds Ib3.1 to Ib3.420 which differ from the compounds Ib1.1 to Ib1.420 in that R¹³ is cyclopentyl.

Most particular preference is also given to the compounds of the formula Ib4, in particular to the compounds Ib4.1 to Ib4.420 which differ from the compounds Ib1.1 to Ib1.420 in that R¹³ is cyclopentyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ib5, in particular to the compounds Ib5.1 to Ib5.420 which differ from the compounds Ib1.1 to Ib1.420 in that R¹³ is cyclohexyl.

Most particular preference is also given to the compounds of the formula Ib6, in particular to the compounds Ib6.1 to Ib6.420 which differ from the compounds Ib1.1 to Ib1.420 in that R¹³ is cyclohexyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ib7, in particular to the compounds Ib7.1 to Ib7.420 which differ from the compounds Ib1.1 to Ib1.420 in that R¹³ is 2-norbornyl.

Most particular preference is also given to the compounds of the formula Ib8, in particular to the compounds Ib8.1 to Ib8.420 which differ from the compounds Ib1.1 to Ib1.420 in that R¹³ is 2-norbornyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ib9, in particular to the compounds Ib9.1 to Ib9.420 which differ from the compounds Ib1.1 to Ib1.420 in that R¹³ is 2-adamantyl.

Most particular preference is also given to the compounds of the formula Ib10, in particular to the compounds Ib10.1 to Ib10.420 which differ from the compounds Ib1.1 to Ib1.420 in that R¹³ is 2-adamantyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ib11, in particular to the compounds Ib11.1 to Ib11.420 which differ from the corresponding compounds Ib1.1 to Ib1.420 in that R¹ is methyl.

Most particular preference is also given to the compounds of the formula Ib12, in particular to the compounds Ib12.1 to Ib12.420 which differ from the corresponding compounds Ib1.1 to Ib1.420 in that R¹ is methyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ib13, in particular to the compounds Ib13.1 to Ib13.420 which differ from the compounds Ib1.1 to Ib1.420 in that R¹ is methyl and R¹³ is cyclopentyl.

Most particular preference is also given to the compounds of the formula Ib14, in particular to the compounds Ib14.1 to Ib14.420 which differ from the compounds Ib1.1 to Ib1.420 in that R¹ is methyl, R¹³ is cyclopentyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ib15, in particular to the compounds Ib15.1 to Ib15.420 which differ from the compounds Ib1.1 to Ib1.420 in that R¹ is methyl and R¹³ is cyclohexyl.

Most particular preference is also given to the compounds of the formula Ib16, in particular to the compounds Ib16.1 to Ib16.420 which differ from the compounds Ib1.1 to Ib1.420 in that R¹ is methyl, R¹³ is cyclohexyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ib17, in particular to the compounds Ib17.1 to Ib17.420 which differ from the compounds Ib1.1 to Ib1.420 in that R¹ is methyl and R¹³ is 2-norbornyl.

Most particular preference is also given to the compounds of the formula Ib18, in particular to the compounds Ib18.1 to Ib18.420 which differ from the compounds Ib1.1 to Ib1.420 in that R¹ is methyl, R¹³ is 2-norbornyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ib19, in particular to the compounds Ib19.1 to Ib19.420 which differ from the compounds Ib1.1 to Ib1.420 in that R¹ is methyl and R¹³ is 2-adamantyl.

Most particular preference is also given to the compounds of the formula Ib20, in particular to the compounds Ib20.1 to Ib20.420 which differ from the compounds Ib1.1 to Ib1.420 in that R¹ is methyl, R¹³ is 2-adamantyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ib21, in particular to the compounds Ib21.1 to Ib21.420 which differ from the corresponding compounds Ib1.1 to Ib1.420 in that R¹ is methoxy.

Most particular preference is also given to the compounds of the formula Ib22, in particular to the compounds Ib22.1 to Ib22.420 which differ from the corresponding compounds Ib1.1 to Ib1.420 in that R¹ is methoxy and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ib23, in particular to the compounds Ib23.1 to Ib23.420 which differ from the compounds Ib1.1 to Ib1.420 in that R¹ is methoxy and R¹³ is cyclopentyl.

Most particular preference is also given to the compounds of the formula Ib24, in particular to the compounds Ib24.1 to Ib24.420 which differ from the compounds Ib1.1 to Ib1.420 in that R¹ is methoxy, R¹³ is cyclopentyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ib25, in particular to the compounds Ib25.1 to Ib25.420 which differ from the compounds Ib1.1 to Ib1.420 in that R¹ is methoxy and R¹³ is cyclohexyl.

Most particular preference is also given to the compounds of the formula Ib26, in particular to the compounds Ib26.1 to Ib26.420 which differ from the compounds Ib1.1 to Ib1.420 in that R¹ is methoxy, R¹³ is cyclohexyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ib27, in particular to the compounds Ib27.1 to Ib27.420 which differ from the compounds Ib1.1 to Ib1.420 in that R¹ is methoxy and R¹³ is 2-norbornyl.

Most particular preference is also given to the compounds of the formula Ib28, in particular to the compounds Ib28.1 to Ib28.420 which differ from the compounds Ib1.1 to Ib1.420 in that R¹ is methoxy, R¹³ is 2-norbornyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ib29, in particular to the compounds Ib29.1 to Ib29.420 which differ from the compounds Ib1.1 to Ib1.420 in that R¹ is methoxy and R¹³ is 2-adamantyl.

Most particular preference is also given to the compounds of the formula Ib30, in particular to the compounds Ib30.1 to Ib30.420 which differ from the compounds Ib1.1 to Ib1.420 in that R¹ is methoxy, R¹³ is 2-adamantyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ic1 (=I where R¹=Cl, R³ and R⁶ or R³ and R⁸ together form a bond, R¹³=cyclo-C₃H₅ and R⁵ and R¹⁴=H), in particular to the compounds Ic1.1-Ic1.720 of Table 3, where the radical definitions are of particular importance for the compounds according to the invention not only in combination with one another but in each case also on their own.

TABLE 3 No. X R² Y R⁴ R⁸ Ic1.1 CH H O SCH₃ OH Ic1.2 CH H O SCH₂CH₃ OH Ic1.3 CH H O SO₂CH₃ OH Ic1.4 CH H O SO₂CH₂CH₃ OH Ic1.5 CH H O SO₂CH(CH₃)₂ OH Ic1.6 CH H O SO₂(CH₂)₂CH₃ OH Ic1.7 CH H O Cl OH Ic1.8 CH H O Br OH Ic1.9 CH H O NO₂ OH Ic1.10 CH H O CHF₂ OH Ic1.11 CH H O CF₃ OH Ic1.12 CH H O OCH₃ OH Ic1.13 CH H O OCH₂CH₃ OH Ic1.14 CH H O OCHF₂ OH Ic1.15 CH H O OCF₃ OH Ic1.16 CH CH₃ O SCH₃ OH Ic1.17 CH CH₃ O SCH₂CH₃ OH Ic1.18 CH CH₃ O SO₂CH₃ OH Ic1.19 CH CH₃ O SO₂CH₂CH₃ OH Ic1.20 CH CH₃ O SO₂CH(CH₃)₂ OH Ic1.21 CH CH₃ O SO₂(CH₂)₂CH₃ OH Ic1.22 CH CH₃ O Cl OH Ic1.23 CH CH₃ O Br OH Ic1.24 CH CH₃ O NO₂ OH Ic1.25 CH CH₃ O CHF₂ OH Ic1.26 CH CH₃ O CF₃ OH Ic1.27 CH CH₃ O OCH₃ OH Ic1.28 CH CH₃ O OCH₂CH₃ OH Ic1.29 CH CH₃ O OCF₂ OH Ic1.30 CH CH₃ O OCF₃ OM Ic1.31 CH CH₂CH₃ O SCH₃ OH Ic1.32 CH CH₂CH₃ O SCH₂CH₃ OH Ic1.33 CH CH₂CH₃ O SO₂CH₃ OH Ic1.34 CH CH₂CH₃ O SO₂CH₂CH₃ OH Ic1.35 CH CH₂CH₃ O SO₂CH(CH₃)₃ OH Ic1.36 CH CH₂CH₃ O SO₂(CH₂)₂CH₃ OH Ic1.37 CH CH₂CH₃ O Cl OH Ic1.38 CH CH₂CH₃ O Br OH Ic1.39 CH CH₂CH₃ O NO₂ OH Ic1.40 CH CH₂CH₃ O CHF₂ OH Ic1.41 CH CH₂CH₃ O CF₃ OH Ic1.42 CH CH₂CH₃ O OCH₃ OH Ic1.43 CH CH₂CH₃ O OCH₂CH₃ OH Ic1.44 CH CH₂CH₃ O OCHF₂ OH Ic1.45 CH CH₂CH₃ O OCF₃ OH Ic1.46 CH CH₂Cl O SCH₃ OH Ic1.47 CH CH₂Cl O SCH₂CH₃ OH Ic1.48 CH CH₂Cl O SO₂CH₃ OH Ic1.49 CH CH₂Cl O SO₂CH₂CH₃ OH Ic1.50 CH CH₂Cl O SO₂CH(CH₃)₂ OH Ic1.51 CH CH₂Cl O SO₂(CH₂)₂CH₃ OH Ic1.52 CH CH₂Cl O Cl OH Ic1.53 CH CH₂Cl O Br OH Ic1.54 CH CH₂Cl O NO₂ OH Ic1.55 CH CH₂Cl O CHF₂ OH Ic1.56 CH CH₂Cl O CF₃ OH Ic1.57 CH CH₂Cl O OCH₃ OH Ic1.58 CH CH₂Cl O OCH₂CH₃ OH Ic1.59 CH CH₂Cl O OCHF₂ OH Ic1.60 CH CH₂Cl O OCF₃ OH Ic1.61 CH H S SCH₃ OH Ic1.62 CH H S SCH₂CH₃ OH Ic1.63 CH H S SO₂CH₃ OH Ic1.64 CH H S SO₂CH₂CH₃ OH Ic1.65 CH H S SO₂CH(CH₃)₂ OH Ic1.66 CH H S SO₂(CH₂)₂CH₃ OH Ic1.67 CH H S Cl OH Ic1.68 CH H S Br OH Ic1.69 CH H S NO₂ OH Ic1.70 CH H S CHF₂ OH Ic1.71 CH H S CF₃ OH Ic1.72 CH H S OCH₃ OH Ic1.73 CH H S OCH₂CH₃ OH Ic1.74 CH H S OCHF₂ OH Ic1.75 CH H S OCF₃ OH Ic1.76 CH CH₃ S SCH₃ OH Ic1.77 CH CH₃ S SCH₂CH₃ OH Ic1.78 CH CH₃ S SO₂CH₃ OH Ic1.79 CH CH₃ S SO₂CH₂CH₃ OH Ic1.80 CH CH₃ S SO₂CH(CH₃)₂ OH Ic1.81 CH CH₃ S SO₂(CH₂)₂CH₃ OH Ic1.82 CH CH₃ S Cl OH Ic1.83 CH CH₃ S Br OH Ic1.84 CH CH₃ S NO₂ OH Ic1.85 CH CH₃ S CHF₂ OH Ic1.86 CH CH₃ S CF₃ OH Ic1.87 CH CH₃ S OCH₃ OH Ic1.88 CH CH₃ S OCH₂CH₃ OH Ic1.89 CH CH₃ S OCHF₂ OH Ic1.90 CH CH₃ S OCF₃ OH Ic1.91 CH CH₂CH₃ S SCH₃ OH Ic1.92 CH CH₂CH₃ S SCH₂CH₃ OH Ic1.93 CH CH₂CH₃ S SO₂CH₃ OH Ic1.94 CH CH₂CH₃ S SO₂CH₂CH₃ OH Ic1.95 CH CH₂CH₃ S SO₂CH(CH₃)₂ OH Ic1.96 CH CH₂CH₃ S SO₂(CH₂)₂CH₃ OH Ic1.97 CH CH₂CH₃ S Cl OH Ic1.98 CH CH₂CH₃ S Br OH Ic1.99 CH CH₂CH₃ S NO₂ OH Ic1.100 CH CH₂CH₃ S CHF₂ OH Ic1.101 CH CH₂CH₃ S CF₃ OH Ic1.102 CH CH₂CH₃ S OCH₃ OH Ic1.103 CH CH₂CH₃ S OCH₂CH₃ OH Ic1.104 CH CH₂CH₃ S OCHF₂ OH Ic1.105 CH CH₂CH₃ S OCF₃ OH Ic1.106 CH CH₂Cl S SCH₃ OH Ic1.107 CH CH₂Cl S SCH₂CH₃ OH Ic1.108 CH CH₂Cl S SO₂CH₃ OH Ic1.109 CH CH₂Cl S SO₂CH₂CH₃ OH Ic1.110 CH CH₂Cl S SO₂CH(CH₃)₂ OH Ic1.111 CH CH₂Cl S SO₂(CH₂)₂CH₃ OH Ic1.112 CH CH₂Cl S Cl OH Ic1.113 CH CH₂Cl S Br OH Ic1.114 CH CH₂Cl S NO₂ OH Ic1.115 CH CH₂Cl S CHF₂ OH Ic1.116 CH CH₂Cl S CF₃ OH Ic1.117 CH CH₂Cl S OCH₃ OH Ic1.118 CH CH₂Cl S OCH₂CH₃ OH Ic1.119 CH CH₂Cl S OCHF₂ OH Ic1.120 CH CH₂Cl S OCF₃ OH Ic1.121 CH H NCH₃ SCH₃ OH Ic1.122 CH H NCH₃ SCH₂CH₃ OH Ic1.123 CH H NCH₃ SO₂CH₃ OH Ic1.124 CH H NCH₃ SO₂CH₂CH₃ OH Ic1.125 CH H NCH₃ SO₂CH(CH₃)₂ OH Ic1.126 CH H NCH₃ SO₂(CH₂)₂CH₃ OH Ic1.127 CH H NCH₃ Cl OH Ic1.128 CH H NCH₃ Br OH Ic1.129 CH H NCH₃ NO₂ OH Ic1.130 CH H NCH₃ CHF₂ OH Ic1.131 CH H NCH₃ CF₃ OH Ic1.132 CH H NCH₃ OCH₃ OH Ic1.133 CH H NCH₃ OCH₂CH₃ OH Ic1.134 CH H NCH₃ OCHF₂ OH Ic1.135 CH H NCH₃ OCF₃ OH Ic1.136 CH CH₃ NCH₃ SCH₃ OH Ic1.137 CH CH₃ NCH₃ SCH₂CH₃ OH Ic1.138 CH CH₃ NCH₃ SO₂CH₃ OH Ic1.139 CH CH₃ NCH₃ SO₂CH₂CH₃ OH Ic1.140 CH CH₃ NCH₃ SO₂CH(CH₃)₂ OH Ic1.141 CH CH₃ NCH₃ SO₂(CH₂)₂CH₃ OH Ic1.142 CH CH₃ NCH₃ Cl OH Ic1.143 CH CH₃ NCH₃ Br OH Ic1.144 CH CH₃ NCH₃ NO₂ OH Ic1.145 CH CH₃ NCH₃ CHF₂ OH Ic1.146 CH CH₃ NCH₃ CF₃ OH Ic1.147 CH CH₃ NCH₃ OCH₃ OH Ic1.148 CH CH₃ NCH₃ OCH₂CH₃ OH Ic1.149 CH CH₃ NCH₃ OCHF₂ OH Ic1.150 CH CH₃ NCH₃ OCF₃ OH Ic1.151 CH CH₂CH₃ NCH₃ SCH₃ OH Ic1.152 CH CH₂CH₃ NCH₃ SCH₂CH₃ OH Ic1.153 CH CH₂CH₃ NCH₃ SO₂CH₃ OH Ic1.154 CH CH₂CH₃ NCH₃ SO₂CH₂CH₃ OH Ic1.155 CH CH₂CH₃ NCH₃ SO₂CH(CH₃)₂ OH Ic1.156 CH CH₂CH₃ NCH₃ SO₂(CH₂)₂CH₃ OH Ic1.157 CH CH₂CH₃ NCH₃ Cl OH Ic1.158 CH CH₂CH₃ NCH₃ Br OH Ic1.159 CH CH₂CH₃ NCH₃ NO₂ OH Ic1.160 CH CH₂CH₃ NCH₃ CHF₂ OH Ic1.161 CH CH₂CH₃ NCH₃ CF₃ OH Ic1.162 CH CH₂CH₃ NCH₃ OCH₃ OH Ic1.163 CH CH₂CH₃ NCH₃ OCH₂CH₃ OH Ic1.164 CH CH₂CH₃ NCH₃ OCHF₂ OH Ic1.165 CH CH₂CH₃ NCH₃ OCF₃ OH Ic1.166 CH CH₂Cl NCH₃ SCH₃ OH Ic1.167 CH CH₂Cl NCH₃ SCH₂CH₃ OH Ic1.168 CH CH₂Cl NCH₃ SO₂CH₃ OH Ic1.169 CH CH₂Cl NCH₃ SO₂CH₂CH₃ OH Ic1.170 CH CH₂Cl NCH₃ SO₂CH(CH₃)₂ OH Ic1.171 CH CH₂Cl NCH₃ SO₂(CH₂)₂CH₃ OH Ic1.172 CH CH₂Cl NCH₃ Cl OH Ic1.173 CH CH₂Cl NCH₃ Br OH Ic1.174 CH CH₂Cl NCH₃ NO₂ OH Ic1.175 CH CH₂Cl NCH₃ CHF₂ OH Ic1.176 CH CH₂Cl NCH₃ CF₃ OH Ic1.177 CH CH₂Cl NCH₃ OCH₃ OH Ic1.178 CH CH₂Cl NCH₃ OCH₂CH₃ OH Ic1.179 CH CH₂Cl NCH₃ OCHF₂ OH Ic1.180 CH CH₂Cl NCH₃ OCF₃ OH Ic1.181 C(CH₃) H O SCH₃ OH Ic1.182 C(CH₃) H O SCH₂CH₃ OH Ic1.183 C(CH₃) H O SO₂CH₃ OH Ic1.184 C(CH₃) H O SO₂CH₂CH₃ OH Ic1.185 C(CH₃) H O SO₂CH(CH₃)₂ OH Ic1.186 C(CH₃) H O SO₂(CH₂)₂CH₃ OH Ic1.187 C(CH₃) H O Cl OH Ic1.188 C(CH₃) H O Br OH Ic1.189 C(CH₃) H O NO₂ OH Ic1.190 C(CH₃) H O CHF₂ OH Ic1.191 C(CH₃) H O CF₃ OH Ic1.192 C(CH₃) H O OCH₃ OH Ic1.193 C(CH₃) H O OCH₂CH₃ OH Ic1.194 C(CH₃) H O OCHF₂ OH Ic1.195 C(CH₃) H O OCF₃ OH Ic1.196 C(CH₃) CH₃ O SCH₃ OH Ic1.197 C(CH₃) CH₃ O SCH₂CH₃ OH Ic1.198 C(CH₃) CH₃ O SO₂CH₃ OH Ic1.199 C(CH₃) CH₃ O SO₂CH₂CH₃ OH Ic1.200 C(CH₃) CH₃ O SO₂CH(CH₃)₂ OH Ic1.201 C(CH₃) CH₃ O SO₂(CH₂)₂CH₃ OH Ic1.202 C(CH₃) CH₃ O Cl OH Ic1.203 C(CH₃) CH₃ O Br OH Ic1.204 C(CH₃) CH₃ O NO₂ OH Ic1.205 C(CH₃) CH₃ O CHF₂ OH Ic1.206 C(CH₃) CH₃ O CF₃ OH Ic1.207 C(CH₃) CH₃ O OCH₃ OH Ic1.208 C(CH₃) CH₃ O OCH₂CH₃ OH Ic1.209 C(CH₃) CH₃ O OCHF₂ OH Ic1.210 C(CH₃) CH₃ O OCF₃ OH Ic1.211 C(CH₃) CH₂CH₃ O SCH₃ OH Ic1.212 C(CH₃) CH₂CH₃ O SCH₂CH₃ OH Ic1.213 C(CH₃) CH₂CH₃ O SO₂CH₃ OH Ic1.214 C(CH₃) CH₂CH₃ O SO₂CH₂CH₃ OH Ic1.215 C(CH₃) CH₂CH₃ O SO₂CH(CH₃)₂ OH Ic1.216 C(CH₃) CH₂CH₃ O SO₂(CH₂)₂CH₃ OH Ic1.217 C(CH₃) CH₂CH₃ O Cl OH Ic1.218 C(CH₃) CH₂CH₃ O Br OH Ic1.219 C(CH₃) CH₂CH₃ O NO₂ OH Ic1.220 C(CH₃) CH₂CH₃ O CHF₂ OH Ic1.221 C(CH₃) CH₂CH₃ O CF₃ OH Ic1.222 C(CH₃) CH₂CH₃ O OCH₃ OH Ic1.223 C(CH₃) CH₂CH₃ O OCH₂CH₃ OH Ic1.224 C(CH₃) CH₂CH₃ O OCHF₂ OH Ic1.225 C(CH₃) CH₂CH₃ O OCF₃ OH Ic1.226 C(CH₃) CH₂Cl O SCH₃ OH Ic1.227 C(CH₃) CH₂Cl O SCH₂CH₃ OH Ic1.228 C(CH₃) CH₂Cl O SO₂CH₃ OH Ic1.229 C(CH₃) CH₂Cl O SO₂CH₂CH₃ OH Ic1.230 C(CH₃) CH₂Cl O SO₂CH(CH₃)₂ OH Ic1.231 C(CH₃) CH₂Cl O SO₂(CH₂)₂CH₃ OH Ic1.232 C(CH₃) CH₂Cl O Cl OH Ic1.233 C(CH₃) CH₂Cl O Br OH Ic1.234 C(CH₃) CH₂Cl O NO₂ OH Ic1.235 C(CH₃) CH₂Cl O CHF₂ OH Ic1.236 C(CH₃) CH₂Cl O CF₃ OH Ic1.237 C(CH₃) CH₂Cl O OCH₃ OH Ic1.238 C(CH₃) CH₂Cl O OCH₂CH₃ OH Ic1.239 C(CH₃) CH₂Cl O OCHF₂ OH Ic1.240 C(CH₃) CH₂Cl O OCF₃ OH Ic1.241 C(CH₃) H S SCH₃ OH Ic1.242 C(CH₃) H S SCH₂CH₃ OH Ic1.243 C(CH₃) H S SO₂CH₃ OH Ic1.244 C(CH₃) H S SO₂CH₂CH₃ OH Ic1.245 C(CH₃) H S SO₂CH(CH₃)₂ OH Ic1.246 C(CH₃) H S SO₂(CH₂)₂CH₃ OH Ic1.247 C(CH₃) H S Cl OH Ic1.248 C(CH₃) H S Br OH Ic1.249 C(CH₃) H S NO₂ OH Ic1.250 C(CH₃) H S CHF₂ OH Ic1.251 C(CH₃) H S CF₃ OH Ic1.252 C(CH₃) H S OCH₃ OH Ic1.253 C(CH₃) H S OCH₂CH₃ OH Ic1.254 C(CH₃) H S OCHF₂ OH Ic1.255 C(CH₃) H S OCF₃ OH Ic1.256 C(CH₃) CH₃ S SCH₃ OH Ic1.257 C(CH₃) CH₃ S SCH₂CH₃ OH Ic1.258 C(CH₃) CH₃ S SO₂CH₃ OH Ic1.259 C(CH₃) CH₃ S SO₂CH₂CH₃ OH Ic1.260 C(CH₃) CH₃ S SO₂CH(CH₃)₂ OH Ic1.261 C(CH₃) CH₃ S SO₂(CH₂)₂CH₃ OH Ic1.262 C(CH₃) CH₃ S Cl OH Ic1.263 C(CH₃) CH₃ S Br OH Ic1.264 C(CH₃) CH₃ S NO₂ OH Ic1.265 C(CH₃) CH₃ S CHF₃ OH Ic1.266 C(CH₃) CH₃ S CF₃ OH Ic1.267 C(CH₃) CH₃ S OCH₃ OH Ic1.268 C(CH₃) CH₃ S OCH₂CH₃ OH Ic1.269 C(CH₃) CH₃ S OCHF₂ OH Ic1.270 C(CH₃) CH₃ S OCF₃ OH Ic1.271 C(CH₃) CH₂CH₃ S SCH₃ OH Ic1.272 C(CH₃) CH₂CH₃ S SCH₂CH₃ OH Ic1.273 C(CH₃) CH₂CH₃ S SO₂CH₃ OH Ic1.274 C(CH₃) CH₂CH₃ S SO₂CH₂CH₃ OH Ic1.275 C(CH₃) CH₂CH₃ S SO₂CH(CH₃)₂ OH Ic1.276 C(CH₃) CH₂CH₃ S SO₂(CH₂)₂CH₃ OH Ic1.277 C(CH₃) CH₂CH₃ S Cl OH Ic1.278 C(CH₃) CH₂CH₃ S Br OH Ic1.279 C(CH₃) CH₂CH₃ S NO₂ OH Ic1.280 C(CH₃) CH₂CH₃ S CHF₂ OH Ic1.281 C(CH₃) CH₂CH₃ S CF₃ OH Ic1.282 C(CH₃) CH₂CH₃ S OCH₃ OH Ic1.283 C(CH₃) CH₂CH₃ S OCH₂CH₃ OH Ic1.284 C(CH₃) CH₂CH₃ S OCHF₂ OH Ic1.285 C(CH₃) CH₂CH₃ S OCF₃ OH Ic1.286 C(CH₃) CH₂Cl S SCH₃ OH Ic1.287 C(CH₃) CH₂Cl S SCH₂CH₃ OH Ic1.288 C(CH₃) CH₂Cl S SO₂CH₃ OH Ic1.289 C(CH₃) CH₂Cl S SO₂CH₂CH₃ OH Ic1.290 C(CH₃) CH₂Cl S SO₂CH(CH₃)₂ OH Ic1.291 C(CH₃) CH₂Cl S SO₂(CH₂)₂CH₃ OH Ic1.292 C(CH₃) CH₂Cl S Cl OH Ic1.293 C(CH₃) CH₂Cl S Br OH Ic1.294 C(CH₃) CH₂Cl S NO₂ OH Ic1.295 C(CH₃) CH₂Cl S CHF₂ OH Ic1.296 C(CH₃) CH₂Cl S CF₃ OH Ic1.297 C(CH₃) CH₂Cl S OCH₃ OH Ic1.298 C(CH₃) CH₂Cl S OCH₂CH₃ OH Ic1.299 C(CH₃) CH₂Cl S OCHF₂ OH Ic1.300 C(CH₃) CH₂Cl S OCF₃ OH Ic1.301 C(CH₃) H NCH₃ SCH₃ OH Ic1.302 C(CH₃) H NCH₃ SCH₂CH₃ OH Ic1.303 C(CH₃) H NCH₃ SO₂CH₃ OH Ic1.304 C(CH₃) H NCH₃ SO₂CH₂CH₃ OH Ic1.305 C(CH₃) H NCH₃ SO₂CH(CH₃)₂ OH Ic1.306 C(CH₃) H NCH₃ SO₂(CH₂)₂CH₃ OH Ic1.307 C(CH₃) H NCH₃ Cl OH Ic1.308 C(CH₃) H NCH₃ Br OH Ic1.309 C(CH₃) H NCH₃ NO₂ OH Ic1.310 C(CH₃) H NCH₃ CHF₂ OH Ic1.311 C(CH₃) H NCH₃ CF₃ OH Ic1.312 C(CH₃) H NCH₃ OCH₃ OH Ic1.313 C(CH₃) H NCH₃ OCH₂CH₃ OH Ic1.314 C(CH₃) H NCH₃ OCHF₂ OH Ic1.315 C(CH₃) H NCH₃ OCF₃ OH Ic1.316 C(CH₃) CH₃ NCH₃ SCH₃ OH Ic1.317 C(CH₃) CH₃ NCH₃ SCH₂CH₃ OH Ic1.318 C(CH₃) CH₃ NCH₃ SO₂CH₃ OH Ic1.319 C(CH₃) CH₃ NCH₃ SO₂CH₂CH₃ OH Ic1.320 C(CH₃) CH₃ NCH₃ SO₂CH(CH₃)₂ OH Ic1.321 C(CH₃) CH₃ NCH₃ SO₂(CH₂)₂CH₃ OH Ic1.322 C(CH₃) CH₃ NCH₃ Cl OH Ic1.323 C(CH₃) CH₃ NCH₃ Br OH Ic1.324 C(CH₃) CH₃ NCH₃ NO₂ OH Ic1.325 C(CH₃) CH₃ NCH₃ CHF₂ OH Ic1.326 C(CH₃) CH₃ NCH₃ CF₃ OH Ic1.327 C(CH₃) CH₃ NCH₃ OCH₃ OH Ic1.328 C(CH₃) CH₃ NCH₃ OCH₂CH₃ OH Ic1.329 C(CH₃) CH₃ NCH₃ OCHF₂ OH Ic1.330 C(CH₃) CH₃ NCH₃ OCF₃ OH Ic1.331 C(CH₃) CH₂CH₃ NCH₃ SCH₃ OH Ic1.332 C(CH₃) CH₂CH₃ NCH₃ SCH₂CH₃ OH Ic1.333 C(CH₃) CH₂CH₃ NCH₃ SO₂CH₂ OH Ic1.334 C(CH₃) CH₂CH₃ NCH₃ SO₂CH₂CH₃ OH Ic1.335 C(CH₃) CH₂CH₃ NCH₃ SO₂CH(CH₂)₂ OH Ic1.336 C(CH₃) CH₂CH₃ NCH₃ SO₂(CH₂)₂CH₃ OH Ic1.337 C(CH₃) CH₂CH₃ NCH₃ Cl OH Ic1.338 C(CH₃) CH₂CH₃ NCH₃ Br OH Ic1.339 C(CH₃) CH₂CH₃ NCH₃ NO₂ OH Ic1.340 C(CH₃) CH₂CH₃ NCH₃ CHF₂ OH Ic1.341 C(CH₃) CH₂CH₃ NCH₃ CF₃ OH Ic1.342 C(CH₃) CH₂CH₃ NCH₃ OCH₃ OH Ic1.343 C(CH₃) CH₂CH₃ NCH₃ OCH₂CH₃ OH Ic1.344 C(CH₃) CH₂CH₃ NCH₃ OCHF₂ OH Ic1.345 C(CH₃) CH₂CH₃ NCH₃ OCF₃ OH Ic1.346 C(CH₃) CH₂Cl NCH₃ SCH₃ OH Ic1.347 C(CH₃) CH₂Cl NCH₃ SCH₂CH₃ OH Ic1.348 C(CH₃) CH₂Cl NCH₃ SO₂CH₃ OH Ic1.349 C(CH₃) CH₂Cl NCH₃ SO₂CH₂CH₃ OH Ic1.350 C(CH₃) CH₂Cl NCH₃ SO₂CH(CH₃)₂ OH Ic1.351 C(CH₃) CH₂Cl NCH₃ SO₂(CH₂)₂CH₃ OH Ic1.352 C(CH₃) CH₂Cl NCH₃ Cl OH Ic1.353 C(CH₃) CH₂Cl NCH₃ Br OH Ic1.354 C(CH₃) CH₂Cl NCH₃ NO₂ OH Ic1.355 C(CH₃) CH₂Cl NCH₃ CHF₂ OH Ic1.356 C(CH₃) CH₂Cl NCH₃ CF₃ OH Ic1.357 C(CH₃) CH₂Cl NCH₃ OCH₃ OH Ic1.358 C(CH₃) CH₂Cl NCH₃ OCH₂CH₃ OH Ic1.359 C(CH₃) CH₂Cl NCH₃ OCHF₂ OH Ic1.360 C(CH₃) CH₂Cl NCH₃ OCF₃ OH Ic1.361 C(CH₂CH₃) H O SCH₃ OH Ic1.362 C(CH₂CH₃) H O SCH₂CH₃ OH Ic1.363 C(CH₂CH₃) H O SO₂CH₃ OH Ic1.364 C(CH₂CH₃) H O SO₂CH₂CH₃ OH Ic1.365 C(CH₂CH₃) H O SO₂CH(CH₃)₂ OH Ic1.366 C(CH₂CH₃) H O SO₂(CH₂)₂CH₃ OH Ic1.367 C(CH₂CH₃) H O Cl OH Ic1.368 C(CH₂CH₃) H O Br OH Ic1.369 C(CH₂CH₃) H O NO₂ OH Ic1.370 C(CH₂CH₃) H O CHF₂ OH Ic1.371 C(CH₂CH₃) H O CF₃ OH Ic1.372 C(CH₂CH₃) H O OCH₃ OH Ic1.373 C(CH₂CH₃) H O OCH₂CH₃ OH Ic1.374 C(CH₂CH₃) H O OCHF₂ OH Ic1.375 C(CH₂CH₃) H O OCF₃ OH Ic1.376 C(CH₂CH₃) CH₃ O SCH₃ OH Ic1.377 C(CH₂CH₃) CH₃ O SCH₂CH₃ OH Ic1.378 C(CH₂CH₃) CH₃ O SO₂CH₃ OH Ic1.379 C(CH₂CH₃) CH₃ O SO₂CH₂CH₃ OH Ic1.380 C(CH₂CH₃) CH₃ O SO₂CH(CH₃)₂ OH Ic1.381 C(CH₂CH₃) CH₃ O SO₂(CH₂)₂CH₃ OH Ic1.382 C(CH₂CH₃) CH₃ O Cl OH Ic1.383 C(CH₂CH₃) CH₃ O Br OH Ic1.384 C(CH₂CH₃) CH₃ O NO₂ OH Ic1.385 C(CH₂CH₃) CH₃ O CHF₂ OH Ic1.386 C(CH₂CH₃) CH₃ O CF₃ OH Ic1.387 C(CH₂CH₃) CH₃ O OCH₃ OH Ic1.388 C(CH₂CH₃) CH₃ O OCH₂CH₃ OH Ic1.389 C(CH₂CH₃) CH₃ O OCHF₂ OH Ic1.390 C(CH₂CH₃) CH₃ O OCF₃ OH Ic1.391 C(CH₂CH₃) CH₂CH₃ O SCH₃ OH Ic1.392 C(CH₂CH₃) CH₂CH₃ O SCH₂CH₃ OH Ic1.393 C(CH₂CH₃) CH₂CH₃ O SO₂CH₃ OH Ic1.394 C(CH₂CH₃) CH₂CH₃ O SO₂CH₂CH₃ OH Ic1.395 C(CH₂CH₃) CH₂CH₃ O SO₂CH(CH₃)₂ OH Ic1.396 C(CH₂CH₃) CH₂CH₃ O SO₂(CH₂)₂CH₃ OH Ic1.397 C(CH₂CH₃) CH₂CH₃ O Cl OH Ic1.398 C(CH₂CH₃) CH₂CH₃ O Br OH Ic1.399 C(CH₂CH₃) CH₂CH₃ O NO₂ OH Ic1.400 C(CH₂CH₃) CH₂CH₃ O CHF₂ OH Ic1.401 C(CH₂CH₃) CH₂CH₃ O CF₃ OH Ic1.402 C(CH₂CH₃) CH₂CH₃ O OCH₃ OH Ic1.403 C(CH₂CH₃) CH₂CH₃ O OCH₂CH₃ OH Ic1.404 C(CH₂CH₃) CH₂CH₃ O OCHF₂ OH Ic1.405 C(CH₂CH₃) CH₂CH₃ O OCF₃ OH Ic1.406 C(CH₂CH₃) CH₂Cl O SCH₃ OH Ic1.407 C(CH₂CH₃) CH₂Cl O SCH₂CH₃ OH Ic1.408 C(CH₂CH₃) CH₂Cl O SO₂CH₃ OH Ic1.409 C(CH₂CH₃) CH₂Cl O SO₂CH₂CH₃ OH Ic1.410 C(CH₂CH₃) CH₂Cl O SO₂CH(CH₃)₂ OH Ic1.411 C(CH₂CH₃) CH₂Cl O SO₂(CH₂)₂CH₃ OH Ic1.412 C(CH₂CH₃) CH₂Cl O Cl OH Ic1.413 C(CH₂CH₃) CH₂Cl O Br OH Ic1.414 C(CH₂CH₃) CH₂Cl O NO₂ OH Ic1.415 C(CH₂CH₃) CH₂Cl O CHF₂ OH Ic1.416 C(CH₂CH₃) CH₂Cl O CF₃ OH Ic1.417 C(CH₂CH₃) CH₂Cl O OCH₃ OH Ic1.418 C(CH₂CH₃) CH₂Cl O OCH₂CH₃ OH Ic1.419 C(CH₂CH₃) CH₂Cl O OCHF₂ OH Ic1.420 C(CH₂CH₃) CH₂Cl O OCF₃ OH Ic1.421 C(CH₂CH₃) H S SCH₃ OH Ic1.422 C(CH₂CH₃) H S SCH₂CH₃ OH Ic1.423 C(CH₂CH₃) H S SO₂CH₃ OH Ic1.424 C(CH₂CH₃) H S SO₂CH₂CH₃ OH Ic1.425 C(CH₂CH₃) H S SO₂CH(CH₃)₂ OH Ic1.426 C(CH₂CH₃) H S SO₂(CH₂)₂CH₃ OH Ic1.427 C(CH₂CH₃) H S Cl OH Ic1.428 C(CH₂CH₃) H S Br OH Ic1.429 C(CH₂CH₃) H S NO₂ OH Ic1.430 C(CH₂CH₃) H S CHF₂ OH Ic1.431 C(CH₂CH₃) H S CF₃ OH Ic1.432 C(CH₂CH₃) H S OCH₃ OH Ic1.433 C(CH₂CH₃) H S OCH₂CH₃ OH Ic1.434 C(CH₂CH₃) H S OCHF₂ OH Ic1.435 C(CH₂CH₃) H S OCF₃ OH Ic1.436 C(CH₂CH₃) CH₃ S SCH₃ OH Ic1.437 C(CH₂CH₃) CH₃ S SCH₂CH₃ OH Ic1.438 C(CH₂CH₃) CH₃ S SO₂CH₃ OH Ic1.439 C(CH₂CH₃) CH₃ S SO₂CH₂CH₃ OH Ic1.440 C(CH₂CH₃) CH₃ S SO₂CH(CH₃)₂ OH Ic1.441 C(CH₂CH₃) CH₃ S SO₂(CH₂)₂CH₃ OH Ic1.442 C(CH₂CH₃) CH₃ S Cl OH Ic1.443 C(CH₂CH₃) CH₃ S Br OH Ic1.444 C(CH₂CH₃) CH₃ S NO₂ OH Ic1.445 C(CH₂CH₃) CH₃ S CHF₂ OH Ic1.446 C(CH₂CH₃) CH₃ S CF₃ OH Ic1.447 C(CH₂CH₃) CH₃ S OCH₃ OH Ic1.448 C(CH₂CH₃) CH₃ S OCH₂CH₃ OH Ic1.449 C(CH₂CH₃) CH₃ S OCHF₂ OH Ic1.450 C(CH₂CH₃) CH₃ S OCF₃ OH Ic1.451 C(CH₂CH₃) CH₂CH₃ S SCH₃ OH Ic1.452 C(CH₂CH₃) CH₂CH₃ S SCH₂CH₃ OH Ic1.453 C(CH₂CH₃) CH₂CH₃ S SO₂CH₃ OH Ic1.454 C(CH₂CH₃) CH₂CH₃ S SO₂CH₂CH₃ OH Ic1.455 C(CH₂CH₃) CH₂CH₃ S SO₂CH(CH₃)₂ OH Ic1.456 C(CH₂CH₃) CH₂CH₃ S SO₂(CH₂)₂CH₃ OH Ic1.457 C(CH₂CH₃) CH₂CH₃ S Cl OH Ic1.458 C(CH₂CH₃) CH₂CH₃ S Br OH Ic1.459 C(CH₂CH₃) CH₂CH₃ S NO₂ OH Ic1.460 C(CH₂CH₃) CH₂CH₃ S CHF₂ OH Ic1.461 C(CH₂CH₃) CH₂CH₃ S CF₃ OH Ic1.462 C(CH₂CH₃) CH₂CH₃ S OCH₃ OH Ic1.463 C(CH₂CH₃) CH₂CH₃ S OCH₂CH₃ OH Ic1.464 C(CH₂CH₃) CH₂CH₃ S OCHF₂ OH Ic1.465 C(CH₂CH₃) CH₂CH₃ S OCF₃ OH Ic1.466 C(CH₂CH₃) CH₂Cl S SCH₃ OH Ic1.467 C(CH₂CH₃) CH₂Cl S SCH₂CH₃ OH Ic1.468 C(CH₂CH₃) CH₂Cl S SO₂CH₃ OH Ic1.469 C(CH₂CH₃) CH₂Cl S SO₂CH₂CH₃ OH Ic1.470 C(CH₂CH₃) CH₂Cl S SO₂CH(CH₃)₂ OH Ic1.471 C(CH₂CH₃) CH₂Cl S SO₂(CH₂)₂CH₃ OH Ic1.472 C(CH₂CH₃) CH₂Cl S Cl OH Ic1.473 C(CH₂CH₃) CH₂Cl S Br OH Ic1.474 C(CH₂CH₃) CH₂Cl S NO₂ OH Ic1.475 C(CH₂CH₃) CH₂Cl S CHF₂ OH Ic1.476 C(CH₂CH₃) CH₂Cl S CF₃ OH Ic1.477 C(CH₂CH₃) CH₂Cl S OCH₃ OH Ic1.478 C(CH₂CH₃) CH₂Cl S OCH₂CH₃ OH Ic1.479 C(CH₂CH₃) CH₂Cl S OCHF₂ OH Ic1.480 C(CH₂CH₃) CH₂Cl S OCF₃ OH Ic1.481 C(CH₂CH₃) H NCH₃ SCH₃ OH Ic1.482 C(CH₂CH₃) H NCH₃ SCH₂CH₃ OH Ic1.483 C(CH₂CH₃) H NCH₃ SO₂CH₃ OH Ic1.484 C(CH₂CH₃) H NCH₃ SO₂CH₂CH₃ OH Ic1.485 C(CH₂CH₃) H NCH₃ SO₂CH(CH₃)₂ OH Ic1.486 C(CH₂CH₃) H NCH₃ SO₂(CH₂)₂CH₃ OH Ic1.487 C(CH₂CH₃) H NCH₃ Cl OH Ic1.488 C(CH₂CH₃) H NCH₃ Br OH Ic1.489 C(CH₂CH₃) H NCH₃ NO₂ OH Ic1.490 C(CH₂CH₃) H NCH₃ CHF₂ OH Ic1.491 C(CH₂CH₃) H NCH₃ CF₃ OH Ic1.492 C(CH₂CH₃) H NCH₃ OCH₃ OH Ic1.493 C(CH₂CH₃) H NCH₃ OCH₂CH₃ OH Ic1.494 C(CH₂CH₃) H NCH₃ OCHF₂ OH Ic1.495 C(CH₂CH₃) H NCH₃ OCF₃ OH Ic1.496 C(CH₂CH₃) CH₃ NCH₃ SCH₃ OH Ic1.497 C(CH₂CH₃) CH₃ NCH₃ SCH₂CH₃ OH Ic1.498 C(CH₂CH₃) CH₃ NCH₃ SO₂CH₃ OH Ic1.499 C(CH₂CH₃) CH₃ NCH₃ SO₂CH₂CH₃ OH Ic1.500 C(CH₂CH₃) CH₃ NCH₃ SO₂CH(CH₃)₂ OH Ic1.501 C(CH₂CH₃) CH₃ NCH₃ SO₂(CH₂)₂CH₃ OH Ic1.502 C(CH₂CH₃) CH₃ NCH₃ Cl OH Ic1.503 C(CH₂CH₃) CH₃ NCH₃ Br OH Ic1.504 C(CH₂CH₃) CH₃ NCH₃ NO₂ OH Ic1.505 C(CH₂CH₃) CH₃ NCH₃ CHF₂ OH Ic1.506 C(CH₂CH₃) CH₃ NCH₃ CF₃ OH Ic1.507 C(CH₂CH₃) CH₃ NCH₃ OCH₃ OH Ic1.508 C(CH₂CH₃) CH₃ NCH₃ OCH₂CH₃ OH Ic1.509 C(CH₂CH₃) CH₃ NCH₃ OCHF₂ OH Ic1.510 C(CH₂CH₃) CH₃ NCH₃ OCF₃ OH Ic1.511 C(CH₂CH₃) CH₂CH₃ NCH₃ SCH₃ OH Ic1.512 C(CH₂CH₃) CH₂CH₃ NCH₃ SCH₂CH₃ OH Ic1.513 C(CH₂CH₃) CH₂CH₃ NCH₃ SO₂CH₃ OH Ic1.514 C(CH₂CH₃) CH₂CH₃ NCH₃ SO₂CH₂CH₃ OH Ic1.515 C(CH₂CH₃) CH₂CH₃ NCH₃ SO₂CH(CH₃)₂ OH Ic1.516 C(CH₂CH₃) CH₂CH₃ NCH₃ SO₂(CH₂)₂CH₃ OH Ic1.517 C(CH₂CH₃) CH₂CH₃ NCH₃ Cl OH Ic1.518 C(CH₂CH₃) CH₂CH₃ NCH₃ Br OH Ic1.519 C(CH₂CH₃) CH₂CH₃ NCH₃ NO₂ OH Ic1.520 C(CH₂CH₃) CH₂CH₃ NCH₃ CHF₂ OH Ic1.521 C(CH₂CH₃) CH₂CH₃ NCH₃ CF₃ OH Ic1.522 C(CH₂CH₃) CH₂CH₃ NCH₃ OCH₃ OH Ic1.523 C(CH₂CH₃) CH₂CH₃ NCH₃ OCH₂CH₃ OH Ic1.524 C(CH₂CH₃) CH₂CH₃ NCH₃ OCHF₂ OH Ic1.525 C(CH₂CH₃) CH₂CH₃ NCH₃ OCF₃ OH Ic1.526 C(CH₂CH₃) CH₂Cl NCH₃ SCH₃ OH Ic1.527 C(CH₂CH₃) CH₂Cl NCH₃ SCH₂CH₃ OH Ic1.528 C(CH₂CH₃) CH₂Cl NCH₃ SO₂CH₃ OH Ic1.529 C(CH₂CH₃) CH₂Cl NCH₃ SO₂CH₂CH₃ OH Ic1.530 C(CH₂CH₃) CH₂Cl NCH₃ SO₂CH(CH₃)₂ OH Ic1.531 C(CH₂CH₃) CH₂Cl NCH₃ SO₂(CH₂)₂CH₃ OH Ic1.532 C(CH₂CH₃) CH₂Cl NCH₃ Cl OH Ic1.533 C(CH₂CH₃) CH₂Cl NCH₃ Br OH Ic1.534 C(CH₂CH₃) CH₂Cl NCH₃ NO₂ OH Ic1.535 C(CH₂CH₃) CH₂Cl NCH₃ CHF₂ OH Ic1.536 C(CH₂CH₃) CH₂Cl NCH₃ CF₃ OH Ic1.537 C(CH₂CH₃) CH₂Cl NCH₃ OCH₃ OH Ic1.538 C(CH₂CH₃) CH₂Cl NCH₃ OCH₂CH₃ OH Ic1.539 C(CH₂CH₃) CH₂Cl NCH₃ OCHF₂ OH Ic1.540 C(CH₂CH₃) CH₂Cl NCH₃ OCF₃ OH Ic1.541 N H O SCH₃ OH Ic1.542 N H O SCH₂CH₃ OH Ic1.543 N H O SO₂CH₃ OH Ic1.544 N H O SO₂CH₂CH₃ OH Ic1.545 N H O SO₂CH(CH₃)₂ OH Ic1.546 N H O SO₂(CH₂)₂CH₃ OH Ic1.547 N H O Cl OH Ic1.548 N H O Br OH Ic1.549 N H O NO₂ OH Ic1.550 N H O CHF₂ OH Ic1.551 N H O CF₃ OH Ic1.552 N H O OCH₃ OH Ic1.553 N H O OCH₂CH₃ OH Ic1.554 N H O OCHF₂ OH Ic1.555 N H O OCF₃ OH Ic1.556 N CH₃ O SCH₃ OH Ic1.557 N CH₃ O SCH₂CH₃ OH Ic1.558 N CH₃ O SO₂CH₃ OH Ic1.559 N CH₃ O SO₂CH₂CH₃ OH Ic1.560 N CH₃ O SO₂CH(CH₃)₂ OH Ic1.561 N CH₃ O SO₂(CH₂)₂CH₃ OH Ic1.562 N CH₃ O Cl OH Ic1.563 N CH₃ O Br OH Ic1.564 N CH₃ O NO₂ OH Ic1.565 N CH₃ O CHF₂ OH Ic1.566 H CH₃ O CF₃ OH Ic1.567 N CH₃ O OCH₃ OH Ic1.568 N CH₃ O OCH₂CH₃ OH Ic1.569 N CH₃ O OCHF₂ OH Ic1.570 N CH₃ O OCF₃ OH Ic1.571 N CH₂CH₃ O SCH₃ OH Ic1.572 N CH₂CH₃ O SCH₂CH₃ OH Ic1.573 N CH₂CH₃ O SO₂CH₃ OH Ic1.574 N CH₂CH₃ O SO₂CH₂CH₃ OH Ic1.575 N CH₂CH₃ O SO₂CH(CH₃)₂ OH Ic1.576 N CH₂CH₃ O SO₂(CH₂)₂CH₃ OH Ic1.577 N CH₂CH₃ O Cl OH Ic1.578 N CH₂CH₃ O Br OH Ic1.579 N CH₂CH₃ O NO₂ OH Ic1.580 N CH₂CH₃ O CHF₂ OH Ic1.581 N CH₂CH₃ O CF₃ OH Ic1.582 N CH₂CH₃ O OCH₃ OH Ic1.583 N CH₂CH₃ O OCH₂CH₃ OH Ic1.584 N CH₂CH₃ O OCHF₂ OH Ic1.585 N CH₂CH₃ O OCF₃ OH Ic1.586 N CH₂Cl O SCH₃ OH Ic1.587 N CH₂Cl O SCH₂CH₃ OH Ic1.588 N CH₂Cl O SO₂CH₃ OH Ic1.589 N CH₂Cl O SO₂CH₂CH₃ OH Ic1.590 N CH₂Cl O SO₂CH(CH₃)₂ OH Ic1.591 N CH₂Cl O SO₂(CH₂)₂CH₃ OH Ic1.592 N CH₂Cl O Cl OH Ic1.593 N CH₂Cl O Br OH Ic1.594 N CH₂Cl O NO₂ OH Ic1.595 N CH₂Cl O CHF₂ OH Ic1.596 N CH₂Cl O CF₃ OH Ic1.597 N CH₂Cl O OCH₃ OH Ic1.598 N CH₂Cl O OCH₂CH₃ OH Ic1.599 N CH₂Cl O OCHF₂ OH Ic1.600 N CH₂Cl O OCF₃ OH Ic1.601 N H S SCH₃ OH Ic1.602 N H S SCH₂CH₃ OH Ic1.603 N H S SO₂CH₃ OH Ic1.604 N H S SO₂CH₂CH₃ OH Ic1.605 N H S SO₂CH(CH₃)₂ OH Ic1.606 N H S SO₂(CH₂)₂CH₃ OH Ic1.607 N H S Cl OH Ic1.608 N H S Br OH Ic1.609 N H S NO₂ OH Ic1.610 N H S CHF₂ OH Ic1.611 N H S CF₃ OH Ic1.612 N H S OCH₃ OH Ic1.613 N H S OCH₂CH₃ OH Ic1.614 N H S OCHF₂ OH Ic1.615 N H S OCF₃ OH Ic1.616 N CH₃ S SCH₃ OH Ic1.617 N CH₃ S SCH₂CH₃ OH Ic1.618 N CH₃ S SO₂CH₃ OH Ic1.619 N CH₃ S SO₂CH₂CH₃ OH Ic1.620 N CH₃ S SO₂CH(CH₃)₂ OH Ic1.621 N CH₃ S SO₂(CH₂)₂CH₃ OH Ic1.622 N CH₃ S Cl OH Ic1.623 N CH₃ S Br OH Ic1.624 N CH₃ S NO₂ OH Ic1.625 N CH₃ S CHF₂ OH Ic1.626 N CH₃ S CF₃ OH Ic1.627 N CH₃ S OCH₃ OH Ic1.628 N CH₃ S OCH₂CH₃ OH Ic1.629 N CH₃ S OCHF₂ OH Ic1.630 N CH₃ S OCF₃ OH Ic1.631 N CH₂CH₃ S SCH₃ OH Ic1.632 N CH₂CH₃ S SCH₂CH₃ OH Ic1.633 N CH₂CH₃ S SO₂CH₃ OH Ic1.634 N CH₂CH₃ S SO₂CH₂CH₃ OH Ic1.635 N CH₂CH₃ S SO₂CH(CH₃)₂ OH Ic1.636 N CH₂CH₃ S SO₂(CH₂)₂CH₃ OH Ic1.637 N CH₂CH₃ S Cl OH Ic1.638 N CH₂CH₃ S Br OH Ic1.639 N CH₂CH₃ S NO₂ OH Ic1.640 N CH₂CH₃ S CHF₂ OH Ic1.641 N CH₂CH₃ S CF₃ OH Ic1.642 N CH₂CH₃ S OCH₃ OH Ic1.643 N CH₂CH₃ S OCH₂CH₃ OH Ic1.644 N CH₂CH₃ S OCHF₂ OH Ic1.645 N CH₂CH₃ S OCF₃ OH Ic1.646 N CH₂Cl S SCH₃ OH Ic1.647 N CH₂Cl S SCH₂CH₃ OH Ic1.648 N CH₂Cl S SO₂CH₃ OH Ic1.649 N CH₂Cl S SO₂CH₂CH₃ OH Ic1.650 N CH₂Cl S SO₂CH(CH₃)₂ OH Ic1.651 N CH₂Cl S SO₂(CH₂)₂CH₃ OH Ic1.652 N CH₂Cl S Cl OH Ic1.653 N CH₂Cl S Br OH Ic1.654 N CH₂Cl S NO₂ OH Ic1.655 N CH₂Cl S CHF₂ OH Ic1.656 H CH₂Cl S CF₃ OH Ic1.657 N CH₂Cl S OCH₃ OH Ic1.658 N CH₂Cl S OCH₂CH₃ OH Ic1.659 N CH₂Cl S OCHF₂ OH Ic1.660 N CH₂Cl S OCF₃ OH Ic1.661 N H NCH₃ SCH₃ OH Ic1.662 N H NCH₃ SCH₂CH₃ OH Ic1.663 N H NCH₃ SO₂CH₃ OH Ic1.664 N H NCH₃ SO₂CH₂CH₃ OH Ic1.665 N H NCH₃ SO₂CH(CH₃)₂ OH Ic1.666 N H NCH₃ SO₂(CH₂)₂CH₃ OH Ic1.667 N H NCH₃ Cl OH Ic1.668 N H NCH₃ Br OH Ic1.669 N H NCH₃ NO₂ OH Ic1.670 N H NCH₃ CHF₂ OH Ic1.671 N H NCH₃ CF₃ OH Ic1.672 N H NCH₃ OCH₃ OH Ic1.673 N H NCH₃ OCH₂CH₃ OH Ic1.674 N H NCH₃ OCHF₂ OH Ic1.675 N H NCH₃ OCF₃ OH Ic1.676 N CH₃ NCH₃ SCH₃ OH Ic1.677 N CH₃ NCH₃ SCH₂CH₃ OH Ic1.678 N CH₃ NCH₃ SO₂CH₃ OH Ic1.679 N CH₃ NCH₃ SO₂CH₂CH₃ OH Ic1.680 N CH₃ NCH₃ SO₂CH(CH₃)₂ OH Ic1.681 N CH₃ NCH₃ SO₂(CH₂)₂CH₃ OH Ic1.682 N CH₃ NCH₃ Cl OH Ic1.683 N CH₃ NCH₃ Br OH Ic1.684 N CH₃ NCH₃ NO₂ OH Ic1.685 N CH₃ NCH₃ CHF₂ OH Ic1.686 N CH₃ NCH₃ CF₃ OH Ic1.687 N CH₃ NCH₃ OCH₃ OH Ic1.688 N CH₃ NCH₃ OCH₂CH₃ OH Ic1.689 N CH₃ NCH₃ OCHF₂ OH Ic1.690 N CH₃ NCH₃ OCF₃ OH Ic1.691 N CH₂CH₃ NCH₃ SCH₃ OH Ic1.692 N CH₂CH₃ NCH₃ SCH₂CH₃ OH Ic1.693 N CH₂CH₃ NCH₃ SO₂CH₃ OH Ic1.694 N CH₂CH₃ NCH₃ SO₂CH₂CH₃ OH Ic1.695 N CH₂CH₃ NCH₃ SO₂CH(CH₃)₂ OH Ic1.696 N CH₂CH₃ NCH₃ SO₂(CH₂)₂CH₃ OH Ic1.697 N CH₂CH₃ NCH₃ Cl OH Ic1.698 N CH₂CH₃ NCH₃ Br OH Ic1.699 N CH₂CH₃ NCH₃ NO₂ OH Ic1.700 N CH₂CH₃ NCH₃ CHF₂ OH Ic1.701 N CH₂CH₃ NCH₃ CF₃ OH Ic1.702 N CH₂CH₃ NCH₃ OCH₃ OH Ic1.703 N CH₂CH₃ NCH₃ OCH₂CH₃ OH Ic1.704 N CH₂CH₃ NCH₃ OCHF₂ OH Ic1.705 N CH₂CH₃ NCH₃ OCF₃ OH Ic1.706 N CH₂Cl NCH₃ SCH₃ OH Ic1.707 N CH₂Cl NCH₃ SCH₂CH₃ OH Ic1.708 N CH₂Cl NCH₃ SO₂CH₃ OH Ic1.709 N CH₂Cl NCH₃ SO₂CH₂CH₃ OH Ic1.710 N CH₂Cl NCH₃ SO₂CH(CH₃)₂ OH Ic1.711 N CH₂Cl NCH₃ SO₂(CH₂)₂CH₃ OH Ic1.712 N CH₂Cl NCH₃ Cl OH Ic1.713 N CH₂Cl NCH₃ Br OH Ic1.714 N CH₂Cl NCH₃ NO₂ OH Ic1.715 N CH₂Cl NCH₃ CHF₂ OH Ic1.716 N CH₂Cl NCH₃ CF₃ OH Ic1.717 N CH₂Cl NCH₃ OCH₃ OH Ic1.718 N CH₂Cl NCH₃ OCH₂CH₃ OH Ic1.719 N CH₂Cl NCH₃ OCHF₂ OH Ic1.720 N CH₂Cl NCH₃ OCF₃ OH

Most particular preference is also given to the compounds of the formula Ic2, in particular to the compounds Ic2.1 to Ic2.720 which differ from the corresponding compounds Ic1.1 to Ic1.720 in that R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ic3, in particular to the compounds Ic3.1 to Ic3.720 which differ from the compounds Ic1.1 to Ic1.720 in that R¹³ is cyclopentyl.

Most particular preference is also given to the compounds of the formula Ic4, in particular to the compounds Ic4.1 to Ic4.720 which differ from the compounds Ic1.1 to Ic1.720 in that R¹³ is cyclopentyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ic5, in particular to the compounds Ic5.1 to Ic5.720 which differ from the compounds Ic1.1 to Ic1.720 in that R¹³ is cyclohexyl.

Most particular preference is also given to the compounds of the formula Ic6, in particular to the compounds Ic6.1 to Ic6.720 which differ from the compounds Ic1.1 to Ic1.720 in that R¹³ is cyclohexyl and R¹⁴ is Methyl.

Most particular preference is also given to the compounds of the formula Ic7, in particular to the compounds Ic7.1 to Ic7.720 which differ from the compounds Ic1.1 to Ic1.720 in that R¹³ is 2-norbornyl.

Most particular preference is also given to the compounds of the formula Ic8, in particular to the compounds Ic8.1 to Ic8.720 which differ from the compounds Ic1.1 to Ic1.720 in that R¹³ is 2-norbornyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ic9, in particular to the compounds Ic9.1 to Ic9.720 which differ from the compounds Ic1.1 to Ic1.720 in that R¹³ is 2-adamantyl.

Most particular preference is also given to the compounds of the formula Ic10, in particular to the compounds Ic10.1 to Ic10.720 which differ from the compounds Ic1.1 to Ic1.720 in that R¹³ is 2-adamantyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ic11, in particular to the compounds Ic11.1 to Ic11.720 which differ from the corresponding compounds Ic1.1 to Ic1.720 in that R¹ is methyl.

Most particular preference is also given to the compounds of the formula Ic12, in particular to the compounds Ic12.1 to Ic12.720 which differ from the corresponding compounds Ic1.1 to Ic1.720 in that R¹ is methyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ic13, in particular to the compounds Ic13.1 to Ic13.720 which differ from the compounds Ic1.1 to Ic1.720 in that R¹ is methyl and R¹³ is cyclopentyl.

Most particular preference is also given to the compounds of the formula Ic14, in particular to the compounds Ic14.1 to Ic14.720 which differ from the compounds Ic1.1 to Ic1.720 in that R¹ is methyl, R¹³ is cyclopentyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ic15, in particular to the compounds Ic15.1 to Ic15.720 which differ from the compounds Ic1.1 to Ic1.720 in that R¹ is methyl and R¹³ is cyclohexyl.

Most particular preference is also given to the compounds of the formula Ic16, in particular to the compounds Ic16.1 to Ic16.720 which differ from the compounds Ic1.1 to Ic1.720 in that R¹ is methyl, R¹³ is cyclohexyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ic17, in particular to the compounds Ic17.1 to Ic17.720 which differ from the compounds Ic1.1 to Ic1.720 in that R¹ is methyl and R¹³ is 2-norbornyl.

Most particular preference is also given to the compounds of the formula Ic18, in particular to the compounds Ic18.1 to Ic18.720 which differ from the compounds Ic1.1 to Ic1.720 in that R¹ is methyl, R¹³ is 2-norbornyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ic19, in particular to the compounds Ic19.1 to Ic19.720 which differ from the compounds Ic1.1 to Ic1.720 in that R¹ is methyl and R¹³ is 2-adamantyl.

Most particular preference is also given to the compounds of the formula Ic20, in particular to the compounds Ic20.1 to Ic20.720 which differ from the compounds Ic1.1 to Ic1.720 in that R¹ is methyl, R¹³ is 2-adamantyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ic21, in particular to the compounds Ic21.1 to Ic21.720 which differ from the corresponding compounds Ic1.1 to Ic1.720 in that R¹ is methoxy.

Most particular preference is also given to the compounds of the formula Ic22, in particular to the compounds Ic22.1 to Ic22.720 which differ from the corresponding compounds Ic1.1 to Ic1.720 in that R¹ is methoxy and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ic23, in particular to the compounds Ic23.1 to Ic23.720 which differ from the compounds Ic1.1 to Ic1.720 in that R¹ is methoxy and R¹³ is cyclopentyl.

Most particular preferenceis also given to the compounds of the formula Ic24, in particular to the compounds Ic24.1 to Ic24.720 which differ from the compounds Ic1.1 to Ic1.720 in that R¹ is methoxy, R¹³ is cyclopentyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ic25, in particular to the compounds Ic25.1 to Ic25.720 which differ from the compounds Ic1.1 to Ic1.720 in that R¹ is methoxy and R¹³ is cyclohexyl.

Most particular preference is also given to the compounds of the formula Ic26, in particular to the compounds Ic26.1 to Ic26.720 which differ from the compounds Ic1.1 to Ic1.720 in that R¹ is methoxy, R¹³ is cyclohexyl and R¹⁴ is methyl.

Most particular preference is also given to the compounds of the formula Ic27, in particular to the compounds Ic27.1 to Ic27.720 which differ from the compounds Ic1.1 to Ic1.720 in that R¹ is methoxy and R¹³ is 2-norbornyl.

Most particular preference is also given to the compounds of the formula Ic28, in particular to the compounds Ic28.1 to Ic28.720 which differ from the compounds Ic1.1 to Ic1.720 in that R¹ is methoxy, R¹³ is 2-norbornyl and R¹⁴ is methyl.

Most particular preference is Also given to the compounds of the formula Ic29, in particular to the compounds Ic29.1 to Ic29.720 which differ from the compounds Ic1.1 to Ic1.720 in that R¹ is methoxy and R¹³ is 2-adamantyl.

Most particular preference is also given to the compounds of the formula Ic30, in particular to the compounds Ic30.1 to Ic30.720 which differ from the compounds Ic1.1 to Ic1.720 in that R¹ is methoxy, R¹³ is 2-adamantyl and R¹⁴ is methyl.

The 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I can be obtained by various routes, for example by the processes below.

Process A

Reaction of pyrazoles of the formula II with an activated benzoic acid IIIα or a benzoic acid IIIβ, which is preferably activated in situ, to give the corresponding acylation product IV, followed by rearrangement, gives compounds of the formula I where R¹²=OH.

L¹ is a nucleophilically displaceable leaving group, such as halogen, for example bromine, chlorine, hetaryl, for example imidazolyl, pyridyl, carboxylate, for example acetate, trifluoroacetate, etc.

The activated benzoic acid can be employed directly, such as in the case of the benzoyl halides, or be generated in situ, for example using dicyclohexylcarbodiimide, triphenylphosphine/azodicarboxylic ester, 2-pyridine disulfide/triphenylphosphine, carbonyldiimidazole, etc.

It may be advantageous to carry out the acylation reaction in the presence of a base. The reactants and the auxiliary base are advantageously employed in this case in equimolar amounts. A slight excess of auxiliary base, for example from 1.2 to 1.5 molar equivalents, based on II, may be advantageous in certain cases.

Suitable auxiliary bases are tertiary alkylamines, pyridine or alkali metal carbonates. Suitable for use as solvents are, for example, chlorinated hydrocarbons, such as methylene chloride, 1,2-dichloroethane, aromatic hydrocarbons, such as toluene, xylene, chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide, dimethyl sulfoxide, or esters, such as ethyl acetate, or mixtures of these.

If the activated carboxylic acid component used is a benzoyl halide, it may be advantageous to cool the reaction mixture to 0-10° C. when adding this reaction partner. The mixture is subsequently stirred at 20-100° C., preferably at 25-50° C., until the reaction has ended. work-up is carried out in a customary manner, for example by pouring the reaction mixture into water and extracting the product of value. Solvents which are particularly suitable for this purpose are methylene chloride, diethyl ether, dimethoxyethane and ethyl acetate. The organic phase is dried and the solvent is removed, after which the crude ester can be employed for the rearrangement without any further purification.

The rearrangement of the esters to the compounds of the formula I is advantageously carried out at 20-40° C. in a solvent and in the presence of a base and, if appropriate, using a cyano compound as catalyst.

Suitable solvents are, for example, acetonitrile, methylene chloride, 1,2-dichlorcethane, dioxane, ethyl acetate, dimethoxyethane, toluene or mixtures of these. Preferred solvents are acetonitrile and dioxane.

Suitable bases are tertiary amines, such as triethylamine or pyridine, or alkali metal carbonates, such as sodium carbonate or potassium carbonate, which are preferably employed in an equimolar amount or an up to four-fold excess, based on the ester. Preference is given to using triethylamine or alkali metal carbonates, preferably in twice the equimolar amount, based on the ester.

Suitable cyano compounds are inorganic cyanides, such as sodium cyanide and potassium cyanide, and organic cyano compounds, such as acetone cyanohydrin and trimethylsilyl cyanide. They are employed in an amount of from 1 to 50 mol percent, based on the ester. Preference is given to using acetone cyanohydrin or trimethylsilyl cyanide, for example in an amount of from 5 to 15, preferably 10, mol percent, based on the ester.

Work-up can be carried out in the manner known per se. The reaction mixture is, for example, acidified with dilute mineral acid, such as 5% strength hydrochloric acid or sulfuric acid, and extracted with an organic solvent, for example methylene chloride or ethyl acetate. The organic extract can be extracted with 5-10% strength alkali metal carbonate solution, for example sodium carbonate or potassium carbonate solution. The aqueous phase is acidified and the resulting precipitate is filtered off with suction and/or extracted with methylene chloride or ethyl acetate, and the mixture is dried and concentrated. (Examples for the preparation of esters of hydroxypyrazoles and for the rearrangement of the esters are given, for example, in EP-A 282 944 and U.S. Pat. No. 4,643,757).

However, it is also possible to generate the “acylation product” IV in situ by reacting a pyrazole of the formula II, or an alkali metal salt thereof with a 3-(heterocyclyl)benzene derivative of the formula V in the presence of carbon monoxide, a catalyst and a base.

L² is a leaving group, such as halogen, for example chlorine, bromine or iodine, or sulfonate, such as mesylate or triflate; preference is given to bromine or triflate.

The “acylation product” IV proceeds to react, directly or indirectly, to give the 1-cycloalkylpyrazolylbenzoyl derivative of the formula I.

Suitable catalysts are palladium-ligand complexes in which the palladium is present in oxidation state 0, metallic palladium, which has optionally been absorbed on a carrier, and preferably palladium(II) salts. The reaction with palladium(II) salts and metallic palladium is preferably carried out in the presence of complex ligands.

An example of a suitable palladium(0)-ligand complex is tetrakis(triphenylphosphine)palladium.

Metallic palladium is preferably absorbed on an inert carrier such as, for example, activated carbon, silica, alumina, barium sulfate or calcium carbonate. The reaction is preferably carried out in the presence of complex ligands such as, for example; triphenylphosphine.

Examples of suitable palladium(II) salts are palladium acetate and palladium chloride. The presence of complex ligands such as, for example, triphenylphosphine is preferred.

Suitable complex ligands for the palladium-ligand complexes, or in whose presence the reaction is preferably carried out with metallic palladium or palladium(II) salts, are tertiary phosphines whose structure is represented by the following formulae:

where z is 1 to 4 and the radicals R^(a) to R^(g) are C₁-C₆-alkyl, C₃-C₆-cycloalkyl, aryl-C₁-C₂-alkyl or, preferably, aryl. Aryl is, for example, naphthyl and unsubstituted or substituted phenyl such as, for example, 2-tolyl and, in particular, unsubstituted phenyl.

The complex palladium salts can be prepared in a manner known per se starting from commercially available palladium salts such as palladium chloride or palladium acetate and the appropriate phosphines such as, for example, triphenylphosphine or 1,2-bis(diphenylphosphino)ethane. Many of the complexed palladium salts are commercially available. Preferred palladium salts are [(R)(+)2,2′-bis(diphenylphosphino)-1,1′-binaphthyl]palladium(II) chloride, bis(triphenylphosphine)palladium(II) acetate and, in particular, bis(triphenylphosphine)palladium(II) chloride.

The palladium catalyst is usually employed in a concentration of from 0.05 to 5 mol %, and preferably 1-3 mol %.

Suitable bases are tertiary amines, such as, for example, N-methylpiperidine, ethyldiisopropylamine, 1,8-bisdimethylaminonaphthalene or, in particular, triethylamine. Also suitable is alkali metal carbonate, such as sodium carbonate or potassium carbonate. However, mixtures of potassium carbonate and triethylamine are also suitable.

In general, from 2 to 4 molar equivalents, in particular 2 molar equivalents, of the alkali metal carbonate, and from 1 to 4 molar equivalents, in particular 2 molar equivalents, of the tertiary amine are employed, based on the 3-(heterocylyl)benzene derivative of the formula V.

Suitable solvents are nitriles, such as benzonitrile and acetonitrile, amides, such as dimethylformide, dimethylacetamide, tetra-C₁-C₄-alkylureas or N-methylpyrrolidone and, preferably, ethers, such as tetrahydrofuran and methyl tert-butyl ethers. Particular preference is given to ethers, such as 1,4-dioxane and dimethoxyethane.

Process B

Compounds of the formula I where R¹²=hydroxyl are obtained by reacting compounds of the formula I where R¹²=hydroxyl with alkylating agents, sulfonylating agents or acylating agents L³-R^(12a)(VI)

L³ is a nucleophilically displaceable leaving group, such as halogen, for example bromine or chlorine, acyloxy, for example acetyloxy or ethylcarbonyloxy, or alkylsulfonyloxy, for example methylsulfonyloxy or trifluoromethylsulfonyloxy.

R^(12a) is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylcarbonyl, phenylsulfonyl or phenylcarbonyl, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy.

The compounds of the formula VI can be employed directly, such as, for example, in the case of the sulfonyl halides or sulfonic anhydrides, or be generated in situ, for example activated sulfonic acids (using sulfonic acid and dicyclohexylcarbonyldiimide, carbonyldiimidazole, etc.).

The starting materials are generally employed in equimolar amounts. However, it may also be advantageous to employ an excess of one or the other component.

If appropriate, it may be advantageous to carry out the reaction in the presence of a base. The reactants and the auxiliary base are advantageously employed in equimolar amounts. An excess of auxiliary base, for example from 1.5 to 3 molar equivalents, based on I, may be advantageous in certain cases.

Suitable auxiliary bases are tertiary alkylamines, such as triethylamine, pyridine, alkali metal carbonates, for example sodium carbonate or potassium carbonate, and alkali metal hydrides, for example sodium hydride. Preference is given to using triethylamine and pyridine.

Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride and 1,2-dichloroethane, aromatic hydrocarbons, for example toluene, xylene, chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran and dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide, dimethyl sulfoxide, or esters, such as ethyl acetate, or mixtures of these.

In general, the reaction temperature is in the range from 0° C. to the boiling point of the reaction mixture.

Work-up can be carried out in the manner known per se to give the product.

The pyrazoles of the formula II used as starting materials are known or can be prepared by processes known per se (for example EP-A 240 001 and J. Prakt. Chem. 315, 383 (1973)). The activated benzoic acids IIIα and the benzoic acids IIIβ are likewise known or can be prepared in the manner known per se (for example WO 96/26206). Furthermore, the 3-(heterocyclyl)benzene derivatives of the formula V are known or can be prepared in the manner known per se (PCT/EP/99/03006).

PREPARATION EXAMPLE 4-[2-Methyl-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyl]-1-cyclopentyl-5-hydroxy-1H-pyrazole (compound 4.6)

1.9 g (9.4 mmol) of dicyclohexylcarbodiimide and 1.3 g (8.8 mmol) of 1-cyclopentyl-5-hydroxy-1H-pyrazole were added to a solution of 2.5 g (8.8 mmol) of 2-methyl-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoic acid in 100 ml of dioxane, and the mixture was stirred at room temperature for 12 hours. Solid components were then filtered off and the filtrate was admixed with 1.5 g (10 mmol) of potassium carbonate and refluxed for 4 hours. The solvent was removed, the residue was then taken up in water and the mixture was washed with ethyl acetate, and then adjusted to pH 3 using 10% strength hydrochloric acid and extracted with methylene chloride. The solvent of the resulting organic phase was distilled off, the residue was taken up in 300 ml of aqueous potassium carbonate solution, insoluble components were filtered off, the pH was adjusted to 3 using 10% strength hydrochloric acid and the resulting precipitate was separated off and dried. Yield: 1.5 g (42% of theory) of 4-[2-methyl-3-(4,5-dihydro-isoxazol-3-yl)-4-methylsulfonylbenzoyl]-1-cyclopentyl-5-hydroxy-1H-pyrazole

M.p.: 135-140° C.

In addition to the compound above, Table 4 lists other 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I which were prepared or are preparable in a similar manner;

TABLE 4 physical data m.p. [° C.]; No. R¹ R² R³ Y R⁴ R¹² R¹³ R¹⁴ ¹H-NMR [δ in ppm] 4.1 Cl H H CH₂ SO₂CH₃ OH cyclopentyl H 192-197 4.2 Cl H H CH₂ SO₂CH₃ OCOC₆H₅ cyclopentyl H 235-240 4.3 Cl H H CH₂ SO₂CH₃ OCO(3-F—C₆H₄) cyclopentyl H 220-225 4.4 Cl H H CH₂ SO₂CH₃ OCH₃ cyclopentyl H 195-200 4.5 Cl H H CH₂ SO₂CH₃ OCH₂CH₃ cyclopentyl H 145-150 4.6 CH₃ H H CH₂ SO₂CH₃ OH cyclopentyl H 135-140 4.7 CH₃ H H CH₂ SO₂CH₃ OCO(3-F—C₆H₄) cyclopentyl H 1.4-2.0 (m, 8H); 2.0(s, 3H); 3.2 (m, 2H); 4.4(m, 2H); 4.8(m, 1H); 7.6-7.8(m, 7H) 4.8 CH₃ H H CH₂ SO₂CH₃ OCH(CH₃)₂ cyclopentyl H 1.2 (d, 6H); 1.4-2.0(m, 8H); 2.7 (s, 3H); 2.9(s, 3H); 3.3(br, 2H); 4.5 (t, 2H), 4.8(br, 1H); 4.9(m, 1H); 7.5 (s, 1H); 7.7(d, 1H); 7.9(d, 1H) 4.9 Cl H H CH₂ SO₂CH₃ OH 2-norbornyl H 135-140 4.10 CH₃ H H CH₂ SO₂CH₃ OH 2-norbornyl H 110-115 4.11 Cl H H CH₂ SO₂CH₃ OCOC₆H₅ 2-norbornyl H 200-205 4.12 Cl H H CH₂ SO₂CH₃ OCO(3-F—C₆H₄) 2-norbornyl H 85-90 4.13 CH₃ H H CH₂ SO₂CH₃ OCOC₆H₅ 2-norbornyl H 1.0-2.5(m, 10H); 2.1(s, 3H); 3.0 (s, 3H); 3.2(t, 2H); 4.2-4.7(m, 3H); 7.4-8.2(m, 8H) 4.14 CH₃ H H CH₂ SO₂CH₃ OCO(3-F—C₆H₄) 2-norbornyl H 1.0-2.6(m, 10H); 2.1(s, 3H); 3.01 (s, 3H); 3.21(t, 2H), 4.3-4.7(m, 3H); 7.4-8.0(m, 7H) 4.15 Cl H H CH₂ SO₂CH₃ OH 2-adamantyl H 120-125 4.16 CH₃ H H CH₂ SO₂CH₃ OH 2-adamantyl H 140-145 4.17 Cl H H CH₂ SO₂CH₃ OH cyclopropyl H 227-228 4.19 OCH₃ H H CH₂ SO₂CH₃ OH cyclopropyl H 197-199 4.19 Cl H H CH₂ SO₂CH₃ OSO₂(4-CH₃—C₆H₄) cyclopropyl H 81-82 4.20 Cl H H CH₂ SO₂CH₃ OCH(CH₃)₂ cyclopropyl H 179-190 4.21 Cl H H CH₂ SO₂CH₃ OCOC₆H₅ cyclopropyl H oil 4.22 Cl H H CH₂ SO₂CH₃ OCO(3-F—C₆H₄) cyclopropyl H 198-200 4.23 OCH₃ H H CH₂ SO₂CH₃ OH cyclopropyl H 160-161 4.24 CH₃ H H CH₂ SO₂CH₃ OH cyclopropyl H 178-179

The 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I and their agriculturally useful salts are suitable, both in the form of isomer mixtures and in the form of the pure isomers, as herbicides. The herbicidal compositions comprising compounds of the formula I control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and harmful grasses in crops such as wheat, rice, maize, soya and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.

Depending on the application method used, the compounds of the formula I, or the herbicidal. compositions comprising them, can additionally be employed in a further number of crop plants for eliminating undesirable plants. Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (S. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds of the formula I may also be used in crops which tolerate the action of herbicides owing to breeding, including genetic engineering methods.

The compounds of the formula I, or the herbicidal compositions comprising them, can be used for example in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly-concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusting agents, materials for broadcasting or granules, by means of spraying, atomizing, dusting, broadcasting or watering. The use forms depend on the intended aims; in any case, they should ensure the finest distribution possible of the active compounds according to the invention.

The herbicidal compositions comprise a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I, and auxiliaries which are customarily used for formulating of crop protection agents.

Essentially, suitable inert auxiliaries include: mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, or strongly polar solvents, e.g. amines such as N-methylpyrrolidone, and water.

Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the substances, either as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates comprising active compound, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.

Suitable surfactants (adjuvants) are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, e.g. ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ether, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene, or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol asters, lignin-sulfite waste liquors or methylcellulose.

Powders, materials for broadcasting and dusting agents can be prepared by mixing or grinding the active compounds together with a solid carrier.

Granules, e.g. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers solid carriers are mineral earths, such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate and ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.

The concentrations of the compounds of the formula I in the ready-to-use preparations can be varied within wide ranges. In general, the formulations comprise about from 0.001 to 98% by weight, preferably 0.01 to 95% by weight of at least one active compound. The active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

The following formulation examples illustrate the preparation of such formulations:

I. 20 parts by weight of compound No. 4.6 are dissolved in a mixture composed of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to 10 mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonate and 5 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.

II. 20 parts by weight of compound no. 4.6 are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.

III. 20 parts by weight of compound No. 4.6 are dissolved in a mixture composed of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction of boiling point 210 to 280° C. and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.

IV. 20 parts by weight of compound No. 4.6 are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalenesulfonate, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives a spray mixture which comprises 0.1% by weight of the active compound.

V. 3 parts by weight of compound No. 4.6 are mixed with 97 parts by weight of finely divided kaolin. This gives a dust which comprises 3% by weight of the active compound.

VI. 20 parts by weight of compound No. 4.6 are mixed intimately with 2 parts by weight of calcium dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenol/urea/formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. This gives a stable oily dispersion.

VII. 1 part by weight of compound No. 4.6 is dissolved in a mixture composed of 70 parts by weight of cyclohexanone, 20 parts by weight of etboxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. This gives a stable emulsion concentrate.

VIII. 1 part by weight of compound No. 4.6 of the formula I is dissolved in a mixture composed of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol® EM 31 (=nonionic emulsifier based on ethoxylated castor oil).

This gives a stable emulsion concentrate.

The compounds of the formula I or the herbicidal compositions can be applied pre- or post-emergence. If the active compounds are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that they come into contact as little as possible, if at all, with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).

The application rates of compound of the formula I are from 0.001 to 3.0, preferably 0.01 to 1.0 kg/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage.

To widen the activity spectrum and to achieve synergistic effects, the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I may be mixed with a large number of representatives of other herbicidal or growth-regulating active compound groups and applied concomitantly. Suitable components for mixtures are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, (het)aryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-((het)aroyl)-1,3-cyclohexanediones, hetaryl aryl ketones, benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates, quinolinecarboxylic acid and its derivatives, chloroacetanilides, cyclohexeneone oxime ether derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils.

It may furthermore be advantageous to apply the compounds of the formula I, alone or else concomitantly in combination with other herbicides, in the form of a mixture with other crop protection agents, for example together with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are employed for treating nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates may also be added.

Use Examples

The herbicidal activity of the 1-cycloalkylpyrazolyl benzoyl derivatives of the formula I was demonstrated by the following greenhouse experiments:

The culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.

For the pre-emergence treatment, the active compounds, which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover causes uniform germination of the test plants, unless this is adversely affected by the active compounds.

For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active compounds which had been suspended or emulsified in water. The test plants were for this purpose either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment. The application rate for the post-emergence treatment was 0.5 or 0.25 kg of a.s. (active substance)/ha.

Depending on the species, the plants were kept at 10-25° C. or 20-35° C. The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.

The evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the aerial parts and 0 means no damage, or normal course of growth.

The plants used in the greenhouse experiments were of the following species:

Scientific name Common name Brachiaria plantaginea alexander grass Chenopodium album lamb's-quarters Echinochloa crus-galli barnyard grass Polygonum persicaria lady's-thumb

At application rates of 0.5 or 0.25 kg/ha, the compound 4.6 (Table 4) showed very good post-emergence action against the abovementioned undesirable plants. 

We claim:
 1. A 1-cycloalkylpyrazolylbenzoyl derivative of the formula I

where X is O; Y is CR¹⁰R¹¹; R¹ is nitro, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfonyl or C₁-C₄-haloalkylsulfonyl; R²,R³,R¹⁰,R¹¹ are hydrogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl; or R³ and R¹¹ together form a bond; R⁴ is halogen, nitro, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfonyl or C₁-C₄-haloalkylsulfonyl; R⁵ is hydrogen, halogen or C₁-C₄-alkyl; R¹² is hydroxyl, C₁-C₆-alkoxy; C₃-C₆-alkenyloxy, C₁-C₆-alkylsulfonyloxy, C₁-C₆-alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; R¹³ is a cyclic ring system containing 3 to 14 ring atoms which may be partially or fully halogenated; or may carry one to three of the following groups: C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy; or may be partially or fully halogenated, and carry one to three of the following groups: C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy; R¹⁴ is hydrogen or C₁-C₄-alkyl; and its agriculturally useful salts.
 2. A 1-cycloalkylpyrazolylbenzoyl derivative of the formula I as claimed in claim 1 where R¹ is nitro, halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy; R⁴ is halogen, nitro, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio or C₁-C₄-alkylsulfonyl.
 3. A 1-cycloalkylpyrazolylbenzoyl derivative of the formula I as claimed in claim 1, where R¹ is halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy; R⁴ is C₁-C₄-alkylsulfonyl; R¹³ is C₃-C₆-cycloalkyl.
 4. A 1-cycloalkylpyrazolylbenzoyl derivative of the formula I as claimed in claim 1, where R⁵ is hydrogen.
 5. A process for preparing 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where R¹²=hydroxyl as claimed in claim 1, which comprises acylating a pyrazole of the formula II

with an activated benzoic acid IIIa or a benzoic acid IIIb,

where the variables X, Y, R¹ to R⁵ and R¹³ to R¹⁴ are as defined in claim 1 and L¹ is a nucleophilically displaceable leaving group, rearranging the acylation product in the presence or the absence of a catalyst to give the compounds of the fornula I where R¹² is hydroxyl, and, optionally, to prepare 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where R¹² hydroxyl by reacting the product with a compound of the formula VI L³—R^(12a)  VI where L3 is a nucleophilically displaceable leaving group; R^(12a) is C₁-C₆₋alkyl, C₃₋C₆-alkenyl, C₁₋C₆₋-alkylsulfonyl, C₁₋C₆₋-alkylcarbonyl, phenylsulfonyl or phenylcarbonyl, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C₁₋C₄₋alkyl, C₁₋C₄₋haloalkyl, C₁₋C₄₋alkoxy or C₁₋C₄₋haloalkoxy.
 6. A composition comprising a herbicidally effective amount of at least one 1-cycloalkylpyrazolylbenzoyl derivative of the formula I or an agriculturally useful salt of I as claimed in claim 1 and auxiliaries which are customarily used for formulating crop protection agents.
 7. A method for controlling undesirable vegetation, which comprises allowing a herbicidally effective amount of at least one 1-cycloalkylpyrazolylbenzoyl derivative of the formula I or an agriculturally useful salt of the compound of formula I as claimed in claim 1 to act on plants, their habitat or seeds, or on their habitat and seeds. 